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Author: Grafiati

Published: 18 May 2024

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1

Zhao, Yating, and Wujiong Xia. "Photochemical C–H bond coupling for (hetero)aryl C(sp2)–C(sp3) bond construction." Organic & Biomolecular Chemistry 17, no. 20 (2019): 4951–63. http://dx.doi.org/10.1039/c9ob00244h.

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This review highlights the recent advances in photochemical (hetero)aryl C(sp²)–C(sp³) bond construction via C–H bond coupling such as (hetero)arylation of C(sp³)–H bonds and alkylation of (hetero)aryl C(sp²)–H bonds.

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2

Hucthagowder, Vishwanathan, Chelsea D. Mullins, Rekha Meyer, Rakesh Nagarajan, John F. DiPersio, Ravi Vij, Michael H. Tomasson, and Shashikant Kulkarni. "Resequencing Analysis of the Human Candidate Ras and Receptor Tyrosine Kinase Gene Family In Multiple Myeloma." Blood 116, no. 21 (November 19, 2010): 301. http://dx.doi.org/10.1182/blood.v116.21.301.301.

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Abstract Abstract 301 Multiple myeloma (MM) is an incurable B-cell malignancy characterized by the clonal proliferation and accumulation of malignant plasma cells in the bone marrow. Despite the growing number of sequencing studies, the comprehensive view of somatic mutations in multiple myeloma is far from clear. One of the most frequently altered gene families in most human cancer is the Ras and the tyrosine kinase (TK) genes, which encode for important regulators of various signal transduction pathways. To uncover the somatic mutation profile of Ras gene and TKs in myeloma, we performed a systematic mutation screening from a selected group of 10 candidate genes in 42 primary myeloma patients. The candidate gene selections were based on the highly altered genes extracted from GEO data sets using Function Express, a data mining and viewer for microarray data. The sequencing of the entire gene region including the promoter and the 3`UTR was performed in the Genome sequencing center at Washington University medical center using the standard resequencing pipeline, from the design of the primers to data output. These data were analyzed with a clinical resequencing pipeline and visualized using the Mutation Viewer software (MV v5.1). We identified 24 nonsynonymous alterations in five genes (KRAS2, PIK3CA, INSR, LTK and MERTK) in our myeloma cohort (Table 1). In particular, we identified the previously reported pathogenic mutation in a KRAS gene and novel somatic mutations in the Kinase family (PIK3CA) that would be expected to cause structural changes. We assessed the frequency plots of the known variants and most but not all are significantly different from the normal data set. The overall results suggest that the germline genetic background besides the somatically acquired mutations may exert an important influence on the prognosis and outcome of the myeloma patient. Our genome-wide resequencing approach thus revealed previously known and novel oncogenic mutations in multiple myeloma, but its relevance needs to be considered in the context of other genetic abnormalities. Table 1: DNA alterations in candidate ras and TK genes in primary multiple myeloma Gene Gene IDa Nucleotide changeb Amino acid change Zygosityc PolyPhen COSMIC KRAS2 3845 c.35 G>A p.G12D Hetero P. Dam Yes KRAS2 3845 c.34 G>T, c.33 T>C p.G12C, A11A Hetero Benign Yes KRAS2 3845 c.183 A>C p.Q61H Hetero P. Dam Yes KRAS2 3845 c.186_194 del p.E62_Y64 Homo PIK3CA 5290 c.928 C>T p.R310C Hetero Yes PIK3CA 5290 c.1173 A>G p.I391M Hetero Benign INSR 3643 c.356 C>T p.A119V Hetero INSR 3643 c.2243 C>T p.S748L Hetero INSR 3643 c.3034 G>A p.V1012M Hetero P. Dam LTK 4058 c.125 G>A p.R42Q Hetero Benign LTK 4058 c.680 C>T p.P227L Hetero LTK 4058 c.728 G>A p.R243Q Hetero LTK 4058 c.1603 G>A p.D535N Hetero MERTK 10461 c.60 A>T p.R20S Hetero Benign MERTK 10461 c.1552 A>G p.I518V Hetero, Homo Benign MERTK 10461 c.1397 G>A p.R466K Hetero, Homo Benign MERTK 10461 c.353 G>A p.S118N Hetero, Homo Benign MERTK 10461 c.2608 G>A p.V870I Hetero Benign MERTK 10461 c.844 G>A p.A282T Hetero Benign MERTK 10461 c.1493 A>G, c.1494 C>T p.N498S Hetero Benign MERTK 10461 c.878 G>A p.R293H Hetero Benign MERTK 10461 c.2593 C>T p.R865W Hetero P. Dam MERTK 10461 c.2069 C>T p.T690I Hetero Benign MERTK 10461 c.2467 G>C p.E823Q Hetero Benign a Gene ID at National center for biotechnology information (http://www.ncbi.nlm.nih.gov/sites/entrez) b del., deletion c Homo, homozygous; hetero, heterozygous Disclosures: No relevant conflicts of interest to declare.

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3

Choy, Pui Ying, Shun Man Wong, Anant Kapdi, and Fuk Yee Kwong. "Recent developments in palladium-catalysed non-directed coupling of (hetero)arene C–H bonds with C–Z (Z = B, Si, Sn, S, N, C, H) bonds in bi(hetero)aryl synthesis." Organic Chemistry Frontiers 5, no. 2 (2018): 288–321. http://dx.doi.org/10.1039/c7qo00693d.

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This review article describes the palladium-catalysed non-directed coupling of (hetero)arene C–H bonds with C_(Ar)–Z (Z = B, Si, Sn, S, N, C, H) bonds for facile bi(hetero)aryl synthesis in the past 10 years.

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4

Xiao, Fang, Jin-Hong Lin, Fei Hao, Xing Zheng, Yu Guo, and Ji-Chang Xiao. "Visible light mediated C–H trifluoromethylation of (hetero)arenes." Organic Chemistry Frontiers 9, no. 7 (2022): 1982–85. http://dx.doi.org/10.1039/d2qo00067a.

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Described herein is an efficient visible light mediated trifluoromethylation of (hetero)arenes using TFSP as a CF3 source. Various aromatic (hetero)cycles could undergo this protocol to give the corresponding trifluoromethylation products.

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5

Ran, You, Yudong Yang, Huansha You, and Jingsong You. "RhCl3-Catalyzed Oxidative C–H/C–H Cross-Coupling of (Hetero)aromatic Sulfonamides with (Hetero)arenes." ACS Catalysis 8, no. 3 (January 30, 2018): 1796–801. http://dx.doi.org/10.1021/acscatal.7b04298.

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6

Verrier, Cécile, Pierrik Lassalas, Laure Théveau, Guy Quéguiner, François Trécourt, Francis Marsais, and Christophe Hoarau. "Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series." Beilstein Journal of Organic Chemistry 7 (November 29, 2011): 1584–601. http://dx.doi.org/10.3762/bjoc.7.187.

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Catalytic direct (hetero)arylation of (hetero)arenes is an attractive alternative to traditional Kumada, Stille, Negishi and Suzuki–Miyaura cross-coupling reactions, notably as it avoids the prior preparation and isolation of (hetero)arylmetals. Developments of this methodology in the oxazole series are reviewed in this article. Methodologies, selectivity, mechanism and future aspects are presented.

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7

Liu, Yahu, Xuebin Liao, and Lu Hu. "Recent Progress in Methylation of (Hetero)Arenes by Cross-Coupling or C–H Activation." Synlett 29, no. 04 (February 5, 2018): 375–82. http://dx.doi.org/10.1055/s-0037-1609093.

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Owing to the ‘magic methyl effect’ on a compound’s physical and biological properties, methylation is a strategy frequently used by medicinal chemists in structure–activity relationship studies or in lead optimization. This article highlights the most recent reported methods for the direct methylation of (hetero)arenes, which mainly involve either C–H functionalization or cross-coupling of methylating reagents with (hetero)aryl halides. Methylation of C–H bonds of (hetero)-arenes, which is atom economical, has been explored by several research groups in recent years. Given the unmatchable availability of (hetero)aryl halides, we believe that Ni-catalyzed methylation using iodomethane or deuterated iodomethane as the methyl source is one of the most convenient methods.

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8

Pahovnik, David, Uroš Uršič, Uroš Grošelj, Anton Meden, Jurij Svete, and Branko Stanovnik. "Synthesis of Dimethyl 1-(Hetero)aryl-4-oxo-1,4-dihydropyridazine- 3,5-dicarboxylates from Dimethyl 3-Oxopentane-1,5-dioates." Zeitschrift für Naturforschung B 63, no. 4 (April 1, 2008): 407–14. http://dx.doi.org/10.1515/znb-2008-0407.

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AbstractDimethyl 3-oxopentane-1,5-dioate (dimethyl acetone-1,3-dicarboxylate) (1) was transformed first with (hetero)arenediazonium salts 3a - j into dimethyl 2-[(hetero)arylhydrazono]pentane-1,5-dioates 4a - j followed by reaction with N,N-dimethylformamide dimethylacetal (DMFDMA) to afford, without isolation of intermediates 5a - j, dimethyl 1-(hetero)aryl-4-oxo-1,4-dihydropyridazine-3,5- dicarboxylates 6a - j. An alternative method represents transformation of 1 with DMFDMA into dimethyl 2-[(dimethylamino)methylidene]-3-oxopentane-1,5-dioate (7) followed by treatment with (hetero)arenediazonium salts 3a - c, j to give pyridazine derivatives 6a - c,j.

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9

Arani, A. Ghorbanpour, and R. Kolahchi. "Exact solution for nonlocal axial buckling of linear carbon nanotube hetero-junctions." Proceedings of the Institution of Mechanical Engineers, Part C: Journal of Mechanical Engineering Science 228, no. 2 (March 25, 2013): 366–77. http://dx.doi.org/10.1177/0954406213483647.

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CNT hetero-junctions offer the possibility of being used in micro-electromechanical systems and nano-electromechanical systems. However, in the present work, nonlocal axial buckling analysis of linear CNT hetero-junctions based on Euler–Bernoulli beam (EBB) model is investigated. In order to mathematically model a linear CNT hetero-junction, a CNT with two segments is considered. The constitutive equations are derived based on the Eringen's theory for various boundary conditions, namely clamped–clamped (C–C), clamped–pinned (C–P) and pinned–pinned (P–P). An analytical approach is applied to obtain the dimensionless buckling load of the CNT hetero-junctions. A detailed parametric study is conducted to elucidate the influences of the small-scale coefficient, homogeneity parameter, boundary conditions and CNT length of each segment on the axial buckling of the linear CNT hetero-junctions. The results indicate that the length of each segment and homogeneity parameter have a significant effect on the buckling load of the CNT hetero-junctions and should therefore be considered in its optimum design. Furthermore, the results are in good agreement with the previous researches.

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10

Gui, Yong-Yuan, Li-Li Liao, Liang Sun, Zhen Zhang, Jian-Heng Ye, Guo Shen, Zhi-Peng Lu, Wen-Jun Zhou, and Da-Gang Yu. "Coupling of C(sp3)–H bonds with C(sp2)–O electrophiles: mild, general and selective." Chemical Communications 53, no. 6 (2017): 1192–95. http://dx.doi.org/10.1039/c6cc09685a.

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11

Guo, Lirong, Fengting Liu, Liying Wang, Hairui Yuan, Lei Feng, Haifeng Lu, and Hongyin Gao. "Transition-metal-free aerobic C–O bond formation via C–N bond cleavage." Organic Chemistry Frontiers 7, no. 9 (2020): 1077–81. http://dx.doi.org/10.1039/d0qo00173b.

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We disclosed a TM-free cascade S_NAr-[3,3] rearrangement–rearomatization process for the efficient construction of NOBIN-type biaryls from readily available (hetero)arylhydroxylamines and aryltrimethylammonium salts under mild conditions.

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12

Wen, Si, Weiwei Lv, Dan Ba, Jing Liu, and Guolin Cheng. "Ruthenium(ii)-catalyzed chemoselective deacylative annulation of 1,3-diones with sulfoxonium ylides via C–C bond activation." Chemical Science 10, no. 39 (2019): 9104–8. http://dx.doi.org/10.1039/c9sc03245b.

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13

Iqbal, S. A., J. Pahl, K. Yuan, and M. J. Ingleson. "Intramolecular (directed) electrophilic C–H borylation." Chemical Society Reviews 49, no. 13 (2020): 4564–91. http://dx.doi.org/10.1039/c9cs00763f.

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14

Ni, Hui-Qi, Phillippa Cooper, and Keary M. Engle. "Recent advances in palladium-catalyzed (hetero)annulation of CC bonds with ambiphilic organo(pseudo)halides." Chemical Communications 57, no. 62 (2021): 7610–24. http://dx.doi.org/10.1039/d1cc02836g.

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15

Tanwar, Lalita, Jonas Börgel, Johannes Lehmann, and Tobias Ritter. "Selective C–H Iodination of (Hetero)arenes." Organic Letters 23, no. 13 (June 11, 2021): 5024–27. http://dx.doi.org/10.1021/acs.orglett.1c01530.

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16

Hirano, Koji, and Masahiro Miura. "Copper-mediated oxidative direct C–C (hetero)aromatic cross-coupling." Chemical Communications 48, no. 87 (2012): 10704. http://dx.doi.org/10.1039/c2cc34659a.

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17

Wei, Kai-Jie, Zheng-jun Quan, Zhang Zhang, Yu-xia Da, and Xi-cun Wang. "Direct C–H heteroarylation of azoles with 1,2-di(pyrimidin-2-yl)disulfides through C–S cleavage of disulfides." RSC Advances 6, no. 81 (2016): 78059–63. http://dx.doi.org/10.1039/c6ra18997k.

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18

Roy, Sourav, Michael G. B. Drew, Antonio Bauzá, Antonio Frontera, and Shouvik Chattopadhyay. "Estimation of conventional C–H⋯π (arene), unconventional C–H⋯π (chelate) and C–H⋯π (thiocyanate) interactions in hetero-nuclear nickel(ii)–cadmium(ii) complexes with a compartmental Schiff base." Dalton Transactions 46, no. 16 (2017): 5384–97. http://dx.doi.org/10.1039/c6dt04906k.

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19

Chupakhin, O. N., A. V. Shchepochkin, and V. N. Charushin. "Atom- and step-economical nucleophilic arylation of azaaromatics via electrochemical oxidative cross C–C coupling reactions." Green Chemistry 19, no. 13 (2017): 2931–35. http://dx.doi.org/10.1039/c7gc00789b.

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A simple and efficient electrochemical method for the synthesis of asymmetrical bi(het)aryls through direct functionalization of the C(sp²)–H bond in azaaromatics with fragments of (hetero)aromatic nucleophiles has been developed.

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20

Irgashev, Roman A., Arseny A. Karmatsky, Gennady L. Rusinov, and Valery N. Charushin. "A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles." Beilstein Journal of Organic Chemistry 11 (June 11, 2015): 1000–1007. http://dx.doi.org/10.3762/bjoc.11.112.

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A short and robust approach for the synthesis of 2-(hetero)aryl substituted thieno[2,3-b]indoles from easily available 1-alkylisatins and acetylated (hetero)arenes has been advanced. The two-step procedure includes the “aldol-crotonic” type of condensation of the starting materials, followed by treatment of the intermediate 3-(2-oxo-2-(hetero)arylethylidene)indolin-2-ones with Lawesson’s reagent. The latter process involves two sequential reactions, namely reduction of the C=C ethylidene double bond of the intermediate indolin-2-ones followed by the Paal–Knorr cyclization, thus affording tricyclic thieno[2,3-b]indoles.

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21

Yang, Tao, Congshan Zhou, Zan Yang, Jiao Li, Jie Hua, and Jianmin Yi. "KI/K2S2O8-Mediated α-C–H Sulfenylation of Carbonyl Compounds with (Hetero)Aryl Thiols." Synlett 28, no. 17 (July 13, 2017): 2325–29. http://dx.doi.org/10.1055/s-0036-1588483.

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A new and facile KI/K2S2O8-mediated α-C–H sulfenylation of carbonyl compounds with (hetero)aryl thiols was developed for the formation of C–S bond at room temperature. This method provided a simple process for the synthesis of β-keto thioethers in moderate to excellent yields. A variety of carbonyl compounds and (hetero)aryl thiols were tolerated in this reaction.

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22

Santiago, Carlos, Nuria Sotomayor, and Esther Lete. "Pd(II)-Catalyzed C-H Acylation of (Hetero)arenes—Recent Advances." Molecules 25, no. 14 (July 16, 2020): 3247. http://dx.doi.org/10.3390/molecules25143247.

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Di(hetero)aryl ketones are important motifs present in natural products, pharmaceuticals or agrochemicals. In recent years, Pd(II)-catalyzed acylation of (hetero)arenes in the presence of an oxidant has emerged as a catalytic alternative to classical acylation methods, reducing the production of toxic metal waste. Different directing groups and acyl sources are being studied for this purpose, although further development is required to face mainly selectivity problems in order to be applied in the synthesis of more complex molecules. Selected recent developments and applications are covered in this review.

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23

Cao, Liming, Yu Hua, Hong-Gang Cheng, and Qianghui Zhou. "C–H hetero-functionalization of arenes through palladacyclopentane-type intermediates." Organic Chemistry Frontiers 8, no. 14 (2021): 3883–914. http://dx.doi.org/10.1039/d0qo01350a.

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24

Liu, Xia, Xin Zhao, Fushun Liang, and Baoyi Ren. "t-BuONa-mediated direct C–H halogenation of electron-deficient (hetero)arenes." Organic & Biomolecular Chemistry 16, no. 6 (2018): 886–90. http://dx.doi.org/10.1039/c7ob03081a.

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25

Yang, Yudong, Jingbo Lan, and Jingsong You. "Oxidative C–H/C–H Coupling Reactions between Two (Hetero)arenes." Chemical Reviews 117, no. 13 (January 13, 2017): 8787–863. http://dx.doi.org/10.1021/acs.chemrev.6b00567.

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26

Qin, Dekun, Jing Wang, Xurong Qin, Chunxia Wang, Ge Gao, and Jingsong You. "Rh(iii)-catalyzed oxime ether-directed heteroarylation of arene through oxidative C–H/C–H cross-coupling." Chemical Communications 51, no. 28 (2015): 6190–93. http://dx.doi.org/10.1039/c5cc00387c.

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A rhodium(iii)-catalyzed dehydrogenative cross-coupling reaction has been developed for the synthesis of bi(hetero)aryl scaffolds by using oxime ethers as the directing group. This protocol features a relatively broad substrate scope and a good tolerance of functional groups.

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27

Zhang, Zuxiao, Leah M. Stateman, and David A. Nagib. "δ C–H (hetero)arylationviaCu-catalyzed radical relay." Chemical Science 10, no. 4 (2019): 1207–11. http://dx.doi.org/10.1039/c8sc04366c.

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A radical relay strategy has been developed to enable selective δ C–H arylation. The approach employs a chiral copper catalyst, which serves the dual roles of generating an N-centered radical to promote intramolecular H-atom transfer, and then intercepting a distal C-centered radical for C–C bond formation with (hetero)aryl boronic acids.

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28

Kona, Chandrababu Naidu, Mahesh N. Patil, and Chepuri V. Ramana. "Gold(i) catalyzed [1,3] O → C rearrangement of benzylvinyl ethers." Organic Chemistry Frontiers 3, no. 4 (2016): 453–56. http://dx.doi.org/10.1039/c5qo00397k.

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29

MIRANDA, E. N. "ON THE CAPACITY OF MULTILAYER NEURAL NETWORKS TRAINED WITH BACKPROPAGATION." International Journal of Neural Systems 10, no. 04 (August 2000): 281–85. http://dx.doi.org/10.1142/s0129065700000247.

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The capacity of a layered neural network for learning hetero-associations is studied numerically as a function of the number M of hidden neurons. We find that there is a sharp change in the learning ability of the network as the number of hetero-associations increases. This fact allows us to define a maximum capacity C for a given architecture. It is found that C grows logarithmically with M.

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30

Knochel, Paul, Maximilian Hofmayer, Jeffrey Hammann, and Gérard Cahiez. "Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling Reactions of Di(hetero)arylmanganese Reagents and Primary and Secondary Alkyl Halides." Synlett 29, no. 01 (August 30, 2017): 65–70. http://dx.doi.org/10.1055/s-0036-1590891.

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An iron-catalyzed cross-coupling between di(hetero)arylmanganese reagents and primary and secondary alkyl halides is reported. No rearrangement of secondary alkyl halides to unbranched products was observed in these C–C bond-forming reactions.

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31

Maurício, Tatiana, Daniela Couto, Diana Lopes, Tiago Conde, Rita Pais, Joana Batista, Tânia Melo, et al. "Differences and Similarities in Lipid Composition, Nutritional Value, and Bioactive Potential of Four Edible Chlorella vulgaris Strains." Foods 12, no. 8 (April 12, 2023): 1625. http://dx.doi.org/10.3390/foods12081625.

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The microalga Chlorella vulgaris is a popular food ingredient widely used in the industry, with an increasing market size and value. Currently, several edible strains of C. vulgaris with different organoleptic characteristics are commercialized to meet consumer needs. This study aimed to compare the fatty acid (FA) and lipid profile of four commercialized strains of C. vulgaris (C-Auto, C-Hetero, C-Honey, and C-White) using gas- and liquid-chromatography coupled to mass-spectrometry approaches, and to evaluate their antioxidant and anti-inflammatory properties. Results showed that C-Auto had a higher lipid content compared to the other strains and higher levels of omega-3 polyunsaturated FAs (PUFAs). However, the C-Hetero, C-Honey, and C-White strains had higher levels of omega-6 PUFAs. The lipidome signature was also different between strains, as C-Auto had a higher content of polar lipids esterified to omega-3 PUFAs, while C-White had a higher content of phospholipids with omega-6 PUFAs. C-Hetero and C-Honey showed a higher content of triacylglycerols. All extracts showed antioxidant and anti-inflammatory activity, highlighting C-Auto with greater potential. Overall, the four strains of C. vulgaris can be selectively chosen as a source of added-value lipids to be used as ingredients in food and nutraceutical applications for different market needs and nutritional requirements.

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32

Tabasso, Silvia, Emanuela Calcio Gaudino, Elisa Acciardo, Maela Manzoli, Agnese Giacomino, and Giancarlo Cravotto. "Microwave-Assisted Dehydrogenative Cross Coupling Reactions in γ-valerolactone with a Reusable Pd/β-cyclodextrin Crosslinked Catalyst." Molecules 24, no. 2 (January 14, 2019): 288. http://dx.doi.org/10.3390/molecules24020288.

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Transition-metal mediated C–H bond activation and functionalization is one of the most straightforward and powerful tools in modern organic synthetic chemistry. Oxidative C–H/C–H coupling reactions between two (hetero)arenes under heterogeneous catalysis may be a valuable means for the production of a plethora of bi(hetero)aryls, and one that adheres to the increasing demand for atom-economic and sustainable chemistry. We have therefore developed a reusable heterogeneous catalytic system, which is based on Pd cross-linked β-cyclodextrin, to perform an efficient microwave-assisted oxidative C–H/C–H cross coupling process between benzothiazoles and methyl thiophene in the presence of green solvents.

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33

Yamada, Tsuyoshi, Jing Jiang, Naoya Ito, Kwihwan Park, Hayato Masuda, Chikara Furugen, Moeka Ishida, Seiya Ōtori, and Hironao Sajiki. "Development of Facile and Simple Processes for the Heterogeneous Pd-Catalyzed Ligand-Free Continuous-Flow Suzuki–Miyaura Coupling." Catalysts 10, no. 10 (October 19, 2020): 1209. http://dx.doi.org/10.3390/catal10101209.

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The Suzuki–Miyaura coupling reaction is one of the most widely utilized C–C bond forming methods to create (hetero)biaryl scaffolds. The continuous-flow reaction using heterogeneous catalyst-packed cartridges is a practical and efficient synthetic method to replace batch-type reactions. A continuous-flow ligand-free Suzuki–Miyaura coupling reaction of (hetero)aryl iodides, bromides, and chlorides with (hetero)aryl boronic acids was developed using cartridges packed with spherical resin (tertiary amine-based chelate resin: WA30)-supported palladium catalysts (7% Pd/WA30). The void space in the cartridge caused by the spherical catalyst structures enables the smooth flow of a homogeneously dissolved reaction solution that consists of a mixture of organic and aqueous solvents and is delivered by the use of a single syringe pump. Clogging or serious backpressure was not observed.

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34

Pradhan, Suman, Sandeep Patel, and Indranil Chatterjee. "Nitrosoarene-catalyzed regioselective aromatic C–H sulfinylation with thiols under aerobic conditions." Chemical Communications 56, no. 37 (2020): 5054–57. http://dx.doi.org/10.1039/d0cc01188f.

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35

Hirano, Koji, and Masahiro Miura. "ChemInform Abstract: Copper-Mediated Oxidative Direct C-C (Hetero)aromatic Cross-Coupling." ChemInform 44, no. 3 (January 15, 2013): no. http://dx.doi.org/10.1002/chin.201303199.

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36

Bhujabal, Yuvraj B., Kamlesh S. Vadagaonkar, and Anant R. Kapdi. "Pd/PTABS: Catalyst for Efficient C−H (Hetero)Arylation of 1,3,4-Oxadiazoles Using Bromo(Hetero)Arenes." Asian Journal of Organic Chemistry 8, no. 2 (January 18, 2019): 289–95. http://dx.doi.org/10.1002/ajoc.201800713.

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37

Pacheco-Benichou, Alexandra, Eugénie Ivendengani, Ioannis K. Kostakis, Thierry Besson, and Corinne Fruit. "Copper-Catalyzed C–H Arylation of Fused-Pyrimidinone Derivatives Using Diaryliodonium Salts." Catalysts 11, no. 1 (December 29, 2020): 28. http://dx.doi.org/10.3390/catal11010028.

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Copper-catalyzed Csp2–Csp2 bond forming reactions through C–H activation are still one of the most useful strategies for the diversification of heterocyclic moieties using various coupling partners. A catalytic protocol for the C–H (hetero)arylation of thiazolo[5,4-f]quinazolin-9(8H)-ones and more generally fused-pyrimidinones using catalyst loading of CuI with diaryliodonium triflates as aryl source under microwave irradiation has been disclosed. The selectivity of the transfer of the aryl group was also disclosed in the case of unsymmetrical diaryliodonium salts. Specific phenylation of valuable fused-pyrimidinones including quinazolinone are provided. This strategy enables a rapid access to an array of various (hetero)arylated N-containing polyheteroaromatics as new potential bioactive compounds.

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38

Barata-Vallejo, Sebastián, and Al Postigo. "Photocatalytic Difluoromethylation Reactions of Aromatic Compounds and Aliphatic Multiple C–C Bonds." Molecules 24, no. 24 (December 6, 2019): 4483. http://dx.doi.org/10.3390/molecules24244483.

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Among the realm of visible light photocatalytic transformations, late-stage difluoromethylation reactions (introduction of difluoromethyl groups in the last stages of synthetic protocols) have played relevant roles as the CF2X group substitutions exert positive impacts on the physical properties of organic compounds including solubility, metabolic stability, and lipophilicity, which are tenets of considerable importance in pharmaceutical, agrochemical, and materials science. Visible-light-photocatalyzed difluoromethylation reactions are shown to be accomplished on (hetero)aromatic and carbon–carbon unsaturated aliphatic substrates under mild and environmentally benign conditions.

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39

Ramanavicius, Simonas, Alla Tereshchenko, Renata Karpicz, Vilma Ratautaite, Urte Bubniene, Audrius Maneikis, Arunas Jagminas, and Arunas Ramanavicius. "TiO2-x/TiO2-Structure Based ‘Self-Heated’ Sensor for the Determination of Some Reducing Gases." Sensors 20, no. 1 (December 21, 2019): 74. http://dx.doi.org/10.3390/s20010074.

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In this research we report the gas-sensing properties of TiO2-x/TiO2-based hetero-structure, which was ‘self-heated’ by current that at constant potential passed through the structure. Amperometric measurements were applied for the evaluation of sensor response towards ethanol, methanol, n-propanol and acetone gases/vapours. The sensitivity towards these gases was based on electrical resistance changes, which were determined by amperometric measurements of current at fixed voltage applied between Pt-based contacts/electrodes deposited on the TiO2-x/TiO2-based layer. X-ray diffraction (XRD) analysis revealed the formation of TiO2-x/TiO2-based hetero-structure, which is mainly based on Ti3O5/TiO2 formed during the hydro-thermal oxidation-based sensing-layer preparation process. Additionally, photoluminescence and time-resolved photoluminescence decay kinetics-based signals of this sensing structure revealed the presence of TiO2 mainly in the anatase phase in the TiO2-x/TiO2-based hetero-structure, which was formed at 400 °C annealing temperature. The evaluation of TiO2-x/TiO2-based gas-sensing layer was performed at several different temperatures (25 °C, 72 °C, 150 °C, 180 °C) and at these temperatures different sensitivity to the aforementioned gaseous materials was determined.

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40

Moon, Youngtaek, Yujeong Jeong, Daehyuk Kook, and Sungwoo Hong. "Rh(iii)-catalyzed direct C–H/C–H cross-coupling of quinones with arenes assisted by a directing group: identification of carbazole quinones as GSKβ inhibitors." Organic & Biomolecular Chemistry 13, no. 13 (2015): 3918–23. http://dx.doi.org/10.1039/c4ob02624a.

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41

Zhang, Tao, Zi-Yu Zhang, Guowei Kang, Tao Sheng, Jie-Lun Yan, Yuan-Bin Yang, Yuxin Ouyang, and Jin-Quan Yu. "Enantioselective remote methylene C−H (hetero)arylation of cycloalkane carboxylic acids." Science 384, no. 6697 (May 17, 2024): 793–98. http://dx.doi.org/10.1126/science.ado1246.

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Stereoselective construction of γ- and δ-stereocenters in carbonyl compounds is a pivotal objective in asymmetric synthesis. Here, we report chiral bifunctional oxazoline-pyridone ligands that enable enantioselective palladium-catalyzed remote γ-C−H (hetero)arylations of free cycloalkane carboxylic acids, which are essential carbocyclic building blocks in organic synthesis. The reaction establishes γ-tertiary and α-quaternary stereocenters simultaneously in up to >99% enantiomeric excess, providing access to a wide range of cyclic chiral synthons and bioactive molecules. The sequential enantioselective editing of two methylene C–H bonds can be achieved by using chiral ligands with opposite configuration to construct carbocycles containing three chiral centers. Enantioselective remote δ-C−H (hetero)arylation is also realized to establish δ-stereocenters that are particularly challenging to access using classical methodologies.

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42

Yin, Xue-Song, Yi-Chen Li, Jun Yuan, Wen-Jia Gu, and Bing-Feng Shi. "Copper(ii)-catalyzed methoxylation of unactivated (hetero)aryl C–H bonds using a removable bidentate auxiliary." Organic Chemistry Frontiers 2, no. 2 (2015): 119–23. http://dx.doi.org/10.1039/c4qo00276h.

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43

Dang, C. V., J. Barrett, M. Villa-Garcia, L. M. Resar, G. J. Kato, and E. R. Fearon. "Intracellular leucine zipper interactions suggest c-Myc hetero-oligomerization." Molecular and Cellular Biology 11, no. 2 (February 1991): 954–62. http://dx.doi.org/10.1128/mcb.11.2.954-962.1991.

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The physiological significance of in vitro leucine zipper interactions was studied by the use of two strategies which detect specific protein-protein interactions in mammalian cells. Fusion genes were constructed which produce chimeric proteins containing leucine zipper domains from several proteins fused either to the DNA-binding domain of the Saccharomyces cerevisiae GAL4 protein or to the transcriptional activation domain of the herpes simplex virus VP16 protein. Previous studies in mammalian cells have demonstrated that a single chimeric polypeptide containing these two domains will activate transcription of a reporter gene present downstream of the GAL4 DNA-binding site. Similarly, if the GAL4 DNA-binding domain of a chimeric protein could be complexed through leucine zipper interactions with the VP16 activation domain of another chimeric protein, then transcriptional activation of the reporter gene would be detected. Using this strategy for detecting leucine zipper interactions, we observed homo-oligomerization between leucine zipper domains of the yeast protein GCN4 and hetero-oligomerization between leucine zipper regions from the mammalian transcriptional regulating proteins c-Jun and c-Fos. In contrast, homo-oligomerization of the leucine zipper domain from c-Myc was not detectable in cells. The inability of the c-Myc leucine zipper to homo-oligomerize strongly in cells was confirmed independently. The second strategy to detect leucine zipper interactions takes advantage of the observation that the addition of nuclear localization sequences to a cytoplasmic protein will allow the cytoplasmic protein to be transported to and retained in the nucleus. Chimeric genes encoding proteins with sequences from a cytoplasmic protein fused either to the GCN4 or c-Myc leucine zipper domains were constructed. Experiments with the c-Myc chimeric protein failed to demonstrate transport of the cytoplasmic marker protein to the nucleus in cells expressing the wild-type c-Myc protein. In contrast, the cytoplasmic marker was translocated into the nucleus when the GCN4 leucine zippers were present on both the cytoplasmic marker and a nuclear protein, presumably as a result of leucine zipper interaction. These results suggest that c-Myc function requires hetero-oligomerization to an as yet undefined factor.

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44

Jafarov, Maarif A., HM Mamedov, and EF Nasirov. "Photo sensivity Hetero junction C-Si/Porous-Si/Zncds." Madridge Journal of Nanotechnology & Nanoscience 4, no. 1 (January 28, 2019): 123–26. http://dx.doi.org/10.18689/mjnn-1000125.

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45

Dang, C. V., J. Barrett, M. Villa-Garcia, L. M. Resar, G. J. Kato, and E. R. Fearon. "Intracellular leucine zipper interactions suggest c-Myc hetero-oligomerization." Molecular and Cellular Biology 11, no. 2 (February 1991): 954–62. http://dx.doi.org/10.1128/mcb.11.2.954.

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The physiological significance of in vitro leucine zipper interactions was studied by the use of two strategies which detect specific protein-protein interactions in mammalian cells. Fusion genes were constructed which produce chimeric proteins containing leucine zipper domains from several proteins fused either to the DNA-binding domain of the Saccharomyces cerevisiae GAL4 protein or to the transcriptional activation domain of the herpes simplex virus VP16 protein. Previous studies in mammalian cells have demonstrated that a single chimeric polypeptide containing these two domains will activate transcription of a reporter gene present downstream of the GAL4 DNA-binding site. Similarly, if the GAL4 DNA-binding domain of a chimeric protein could be complexed through leucine zipper interactions with the VP16 activation domain of another chimeric protein, then transcriptional activation of the reporter gene would be detected. Using this strategy for detecting leucine zipper interactions, we observed homo-oligomerization between leucine zipper domains of the yeast protein GCN4 and hetero-oligomerization between leucine zipper regions from the mammalian transcriptional regulating proteins c-Jun and c-Fos. In contrast, homo-oligomerization of the leucine zipper domain from c-Myc was not detectable in cells. The inability of the c-Myc leucine zipper to homo-oligomerize strongly in cells was confirmed independently. The second strategy to detect leucine zipper interactions takes advantage of the observation that the addition of nuclear localization sequences to a cytoplasmic protein will allow the cytoplasmic protein to be transported to and retained in the nucleus. Chimeric genes encoding proteins with sequences from a cytoplasmic protein fused either to the GCN4 or c-Myc leucine zipper domains were constructed. Experiments with the c-Myc chimeric protein failed to demonstrate transport of the cytoplasmic marker protein to the nucleus in cells expressing the wild-type c-Myc protein. In contrast, the cytoplasmic marker was translocated into the nucleus when the GCN4 leucine zippers were present on both the cytoplasmic marker and a nuclear protein, presumably as a result of leucine zipper interaction. These results suggest that c-Myc function requires hetero-oligomerization to an as yet undefined factor.

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46

Meucci, Elizabeth A., Shay N. Nguyen, Nicole M. Camasso, Eugene Chong, Alireza Ariafard, Allan J. Canty, and Melanie S. Sanford. "Nickel(IV)-Catalyzed C–H Trifluoromethylation of (Hetero)arenes." Journal of the American Chemical Society 141, no. 32 (August 5, 2019): 12872–79. http://dx.doi.org/10.1021/jacs.9b06383.

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47

Hayrapetyan, Davit, Raja K. Rit, Markus Kratz, Kristina Tschulik, and Lukas J. Gooßen. "Electrochemical C−H Cyanation of Electron-Rich (Hetero)Arenes." Chemistry - A European Journal 24, no. 44 (July 10, 2018): 11288–91. http://dx.doi.org/10.1002/chem.201802247.

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48

Hamzehloo, Majid, Akram Hosseinian, Saeideh Ebrahimiasl, Aazam Monfared, and Esmail Vessally. "Direct C-H trifluoromethylthiolation of (hetero)arenes: A review." Journal of Fluorine Chemistry 224 (August 2019): 52–60. http://dx.doi.org/10.1016/j.jfluchem.2019.05.004.

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49

Bao, Lei, Hongxiang Yang, Beibei Zhan, and Xiaheng Zhang. "Photoinduced Bi-catalyzed C–H trifluoromethylation of (hetero)arenes." Chem Catalysis 4, no. 1 (January 2024): 100877. http://dx.doi.org/10.1016/j.checat.2023.100877.

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50

Albano, Gianluigi, Angela Punzi, Maria Annunziata M. Capozzi, and Gianluca M. Farinola. "Sustainable protocols for direct C–H bond arylation of (hetero)arenes." Green Chemistry 24, no. 5 (2022): 1809–94. http://dx.doi.org/10.1039/d1gc03168f.

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A comprehensive and critical overview of the sustainable strategies for direct C–H bond arylation of (hetero)arenes, based on the use of recoverable catalysts, sustainable solvents and non-conventional energy sources, has been performed.

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