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Journal articles on the topic 'Borylation reaction'

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Author: Grafiati
Published: 6 September 2023

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1

Chattopadhyay, Buddhadeb, Mirja Md Mahamudul Hassan, Md Emdadul Hoque, Sayan Dey, Saikat Guria, and Brindaban Roy. "Iridium-Catalyzed Site-Selective Borylation of 8-Arylquinolines." Synthesis 53, no. 18 (May 11, 2021): 3333–42. http://dx.doi.org/10.1055/a-1506-3884.

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AbstractWe report a convenient method for the highly site-selective borylation of 8-arylquinoline. The reaction proceeds smoothly in the presence of a catalytic amount of [Ir(OMe)(cod)]2 and 2-phenylpyridine derived ligand using bis(pinacolato)diborane as the borylating agent. The reactions occur with high selectivity with many functional groups, providing a series of borylated 8-aryl quinolines with good to excellent yield and excellent selectivity. The borylated compounds formed in this method can be transformed into various important synthons by using known transformations.
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2

Iwamoto, Hiroaki, Koji Kubota, Eiji Yamamoto, and Hajime Ito. "Copper(i)-catalyzed carbon–halogen bond-selective boryl substitution of alkyl halides bearing terminal alkene moieties." Chemical Communications 51, no. 47 (2015): 9655–58. http://dx.doi.org/10.1039/c5cc02760h.

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The carbon–halogen bond-selective borylation of alkyl halides bearing terminal CC double bonds has been achieved using a copper(i) catalyst. This reaction represents a useful complementary approach to conventional procedures for the borylative cyclization reported in our previous work.
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3

Xie, Jian-bo, Jian Luo, Timothy R. Winn, David B. Cordes, and Guigen Li. "Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines." Beilstein Journal of Organic Chemistry 10 (March 31, 2014): 746–51. http://dx.doi.org/10.3762/bjoc.10.69.

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A new approach to the anticancer drug Velcade was developed by performing asymmetric borylation of an imine anchored with a chiral N-phosphinyl auxiliary. Throughout the 7-step synthesis, especially in the imine’s synthesis and in the asymmetric borylation reactions, operations and work-up were conducted in simple and easy ways without any column chromatographic purification, which defines the GAP (group-assisted purification) chemistry concept. It was found that the optically pure isomer (dr > 99:1) can be readily obtained by washing the crude mixture of the asymmetric borylation reaction with hexane; the chiral N-phosphinyl auxiliary can be easily recovered after deprotection is finished. Several other N-phosphinylimines were also investigated for the asymmetric borylation reaction. The absolute configuration of the borylation product was confirmed by single crystal X-ray diffraction analysis.
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4

Leon, Noel J., Hsien-Cheng Yu, Thomas J. Mazzacano, and Neal P. Mankad. "Pursuit of C–H Borylation Reactions with Non-Precious Heterobimetallic Catalysts: Hypothesis-Driven Variations on a Design Theme." Synlett 31, no. 02 (November 27, 2019): 125–32. http://dx.doi.org/10.1055/s-0039-1691504.

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This article presents a retrospective account of our group’s heterobinuclear (NHC)Cu-[MCO] catalyst design concept (NHC = N-heterocyclic carbene, [MCO] = metal carbonyl anion), the discovery of its application towards UV-light-induced dehydrogenative borylation of unactivated arenes, and the subsequent pursuit of thermal reaction conditions through structural modifications of the catalysts. The account highlights advantages of using a hypothesis-driven catalyst design approach that, while often fruitless with regard to the target transformation in this case, nonetheless vastly expanded the set of heterobinuclear catalysts available for other applications. In other words, curiosity-driven research conducted in a rational manner often provides valuable products with unanticipated applications, even if the primary objective is viewed to have failed.1 Introduction to Heterobinuclear Catalysts for C–H Borylation2 Pursuit of Thermal Borylation Conditions3 Catalysts beyond Copper Carbenes4 Conclusions
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5

Britton, Luke, Jamie H. Docherty, Andrew P. Dominey, and Stephen P. Thomas. "Iron-Catalysed C(sp2)-H Borylation Enabled by Carboxylate Activation." Molecules 25, no. 4 (February 18, 2020): 905. http://dx.doi.org/10.3390/molecules25040905.

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Arene C(sp2)-H bond borylation reactions provide rapid and efficient routes to synthetically versatile boronic esters. While iridium catalysts are well established for this reaction, the discovery and development of methods using Earth-abundant alternatives is limited to just a few examples. Applying an in situ catalyst activation method using air-stable and easily handed reagents, the iron-catalysed C(sp2)-H borylation reactions of furans and thiophenes under blue light irradiation have been developed. Key reaction intermediates have been prepared and characterised, and suggest two mechanistic pathways are in action involving both C-H metallation and the formation of an iron boryl species.
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6

Ji, Hong, Li-Yang Wu, Jiang-Hong Cai, Guo-Rong Li, Na-Na Gan, and Zhao-Hua Wang. "Room-temperature borylation and one-pot two-step borylation/Suzuki–Miyaura cross-coupling reaction of aryl chlorides." RSC Advances 8, no. 25 (2018): 13643–48. http://dx.doi.org/10.1039/c8ra01381k.

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7

Pinet, Sandra, Mathieu Pucheault, Virginie Liautard, and Mégane Debiais. "Radical Metal-Free Borylation of Aryl Iodides." Synthesis 49, no. 21 (May 29, 2017): 4759–68. http://dx.doi.org/10.1055/s-0036-1588431.

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A simple metal-free borylation of aryl iodides mediated by a fluoride sp2–sp3 diboron adduct is described. The reaction conditions are compatible with various functional groups. Electronic effects of substituents do not affect the borylation while steric hindrance does. The reaction proceeds via a radical mechanism in which pyridine serves to stabilize the boryl radicals, generated in situ.
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8

Li, Bingru, Huayu Liang, Arumugam Vignesh, Xiaoyu Zhou, Yan Liu, and Zhuofeng Ke. "Updated Progress of the Copper-Catalyzed Borylative Functionalization of Unsaturated Molecules." Molecules 28, no. 5 (February 28, 2023): 2252. http://dx.doi.org/10.3390/molecules28052252.

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Borylation has become a powerful method to synthesize organoboranes as versatile building blocks in organic synthesis, medicinal chemistry, and materials science. Copper-promoted borylation reactions are extremely attractive due to the low cost and non-toxicity of the copper catalyst, mild reaction conditions, good functional group tolerance, and convenience in chiral induction. In this review, we mainly updated recent advances (from 2020 to 2022) in the synthetic transformations in C=C/C≡C multiple bonds, and C=E multiple bonds mediated by copper boryl systems.
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9

Geier, Stephen J., and Stephen A. Westcott. "Dehydrogenative borylation: the dark horse in metal-catalyzed hydroborations and diborations?" Reviews in Inorganic Chemistry 35, no. 2 (June 1, 2015): 69–79. http://dx.doi.org/10.1515/revic-2014-0008.

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AbstractMetal-catalyzed hydroborations and diborations frequently give “unwanted” side products arising from a competing dehydrogenative borylation reaction. While catalyst development initially focused on avoiding this “deleterious” pathway, fine tuning of a catalyst system could provide an efficient method to generate unsaturated alkenylboronate esters, synthetically valuable synthons for the Suzuki-Miyaura cross-coupling reaction. The aim of this review is to highlight the history and development of the dehydrogenative borylation reaction in the metal-catalyzed synthesis of alkenylboronate esters.
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10

Steven, Alan. "Micelle-Mediated Chemistry in Water for the Synthesis of Drug Candidates." Synthesis 51, no. 13 (May 21, 2019): 2632–47. http://dx.doi.org/10.1055/s-0037-1610714.

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Micellar reaction conditions, in a predominantly aqueous medium, have been developed for transformations commonly used by synthetic chemists working in the pharmaceutical industry to discover and develop drug candidates. The reactions covered in this review are the Suzuki–Miyaura, Miyaura borylation, Sonogashira coupling, transition-metal-catalysed CAr–N coupling, SNAr, amidation, and nitro reduction. Pharmaceutically relevant examples of these applications will be used to show how micellar conditions can offer advantages in yield, operational ease, amount of waste generated, transition-metal catalyst loading, and safety over the use of organic solvents, irrespective of the setting in which they are used.1 Introduction2 Micelles as Solubilising Agents3 Micelles as Nanoreactors4 Designer Surfactants5 A Critical Evaluation of the Case for Chemistry in Micelles6 Scope of Review7 Suzuki–Miyaura Coupling8 Miyaura Borylation9 Sonogashira Coupling10 Transition-Metal-Catalysed CAr–N Couplings11 SNAr12 Amidation13 Nitro Reduction14 Micellar Sequences15 Summary and Outlook
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11

Roesner, Stefan, and Varinder K. Aggarwal. "Enantioselective synthesis of (R)-tolterodine using lithiation/borylation–protodeboronation methodology." Canadian Journal of Chemistry 90, no. 11 (November 2012): 965–74. http://dx.doi.org/10.1139/v2012-069.

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The synthesis of the pharmaceutical (R)-tolterodine is reported using lithiation/borylation–protodeboronation of a homoallyl carbamate as the key step. This step was tested with two permutations: an electron-neutral aryl Li-carbamate reacting with an electron-rich boronic ester and an electron-rich aryl Li-carbamate reacting with an electron-neutral boronic ester. It was found that the latter arrangement was considerably better than the former. Further improvements were achieved using magnesium bromide in methanol leading to a process that gave high yield and high enantioselectivity in the lithiation/borylation reaction. The key step was used in an efficient synthesis of (R)-tolterodine in a total of eight steps in a 30% overall yield and 90% ee.
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12

Cai, Mingzhong, Bin Huang, Chengkai Luo, and Caifeng Xu. "Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Boryl­ation of Aryl Chlorides: Practical Access to Aryl Boronates." Synthesis 54, no. 05 (November 22, 2021): 1339–46. http://dx.doi.org/10.1055/s-0037-1610787.

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AbstractPd2dba3/XPhos in poly(ethylene glycol) (PEG-2000) is shown to be a highly stable and efficient catalyst for the borylation of aryl chlorides with bis(pinacolato)diboron. The borylation reaction proceeds smoothly at 110 °C, delivering a wide variety of aryl boronates in good to excellent yields with high functional group tolerance. The crude products were easily isolated via simple extraction of the reaction mixture with cyclohexane. Moreover, both expensive Pd2dba3 and XPhos in PEG-2000 system could be readily recycled and reused more than six times without loss of catalytic efficiency.
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13

Li, Dai-Yu, Rui-Mu Yu, Jin-Ping Li, Deng-Feng Yang, Qi Pang, and Hong-Liang Li. "The Improved para-Selective C(sp2)-H Borylation of Anisole Derivatives Enabled by Bulky Lewis Acid." Catalysts 13, no. 8 (August 9, 2023): 1193. http://dx.doi.org/10.3390/catal13081193.

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An improved para-selective C(sp2)-H borylation of anisole derivatives is described. The selective borylation is probably dominated by the change in electron density on the aromatic ring when a Lewis acid is coordinated with an anisole substrate. In addition, a sterically hindered bipyridyl ligand used in the reaction also favors para-selectivity. With this strategy, it has been demonstrated that the ratio of para-borylated products could be dramatically improved. The reaction proceeds at a milder temperature, and most substrates display moderate to good site-selectivity.
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14

Pan, Zilong, Luhua Liu, Senmiao Xu, and Zhenlu Shen. "Ligand-free iridium-catalyzed regioselective C–H borylation of indoles." RSC Advances 11, no. 10 (2021): 5487–90. http://dx.doi.org/10.1039/d0ra10211c.

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15

Welle, Alexandre, Virginie Cirriez, and Olivier Riant. "Copper catalyzed tandem conjugated borylation–aldol reaction." Tetrahedron 68, no. 17 (April 2012): 3435–43. http://dx.doi.org/10.1016/j.tet.2011.07.062.

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16

Motokura, Ken, and Kyogo Maeda. "Recent Advances in Heterogeneous Ir Complex Catalysts for Aromatic C–H Borylation." Synthesis 53, no. 18 (April 9, 2021): 3227–34. http://dx.doi.org/10.1055/a-1478-6118.

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AbstractAromatic C–H borylation catalyzed by an Ir complex is among the most powerful methods for activating inert bonds. The products, i.e., arylboronic acids and their esters, are usable chemicals for the Suzuki–Miyaura cross-coupling reaction, and significant effort has been directed toward the development of homogeneous catalysis chemistry. In this short review, we present a recent overview of current heterogeneous Ir-complex catalyst developments for aromatic C–H borylation. Not only have Ir complexes been immobilized on support surfaces with phosphine and bipyridine ligands, but Ir complexes incorporated within solid materials have also been developed as highly active and reusable heterogeneous Ir catalysts. Their catalytic activities and stabilities strongly depend on their surface structures, including linker length and ligand structure.1 Introduction and Homogeneous Ir Catalysis2 Heterogeneous Ir Complex Catalysts for C–H Borylation Reactions3 Other Heterogeneous Metal Complex Catalysts for C–H Borylation Reactions4 Summary and Outlook
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17

Ping, Yifan, Taiwei Chang, Kang Wang, Jingfeng Huo, and Jianbo Wang. "Palladium-catalyzed oxidative borylation of conjugated enynones through carbene migratory insertion: synthesis of furyl-substituted alkenylboronates." Chemical Communications 55, no. 1 (2019): 59–62. http://dx.doi.org/10.1039/c8cc09024f.

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18

Lu, Haiyan, Xiumei Yang, Liwei Zhou, Wenguang Li, Guobo Deng, Yuan Yang, and Yun Liang. "Palladium-catalyzed domino Heck-disilylation and -borylation of alkene-tethered 2-(2-halophenyl)-1H-indoles: access to diverse disilylated and borylated indolo[2,1-a]isoquinolines." Organic Chemistry Frontiers 7, no. 15 (2020): 2016–21. http://dx.doi.org/10.1039/d0qo00492h.

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19

Chen, You, Hui Peng, Yun-Xiao Pi, Tong Meng, Ze-Yu Lian, Meng-Qi Yan, Yan Liu, Sheng-Hua Liu, and Guang-Ao Yu. "Efficient phosphine ligands for the one-pot palladium-catalyzed borylation/Suzuki–Miyaura cross-coupling reaction." Organic & Biomolecular Chemistry 13, no. 11 (2015): 3236–42. http://dx.doi.org/10.1039/c4ob02436b.

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20

Kidonakis, Marios, Michael Fragkiadakis, and Manolis Stratakis. "β-Borylation of conjugated carbonyl compounds with silylborane or bis(pinacolato)diboron catalyzed by Au nanoparticles." Organic & Biomolecular Chemistry 18, no. 43 (2020): 8921–27. http://dx.doi.org/10.1039/d0ob01806f.

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β-Borylation occurs in the Au/TiO2-catalysed reaction between the silylborane Me2PhSiBpin and conjugated carbonyl compounds, in contrast to the so far known analogous reaction catalysed by other metals, where β-silylation occurs instead.
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21

Wang, Jianbo. "When diazo compounds meet with organoboron compounds." Pure and Applied Chemistry 90, no. 4 (March 28, 2018): 617–23. http://dx.doi.org/10.1515/pac-2017-0713.

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AbstractTransition-metal free reactions of diazo compounds with organoboron compounds provide some unique approaches for the formation of C–C, C–B and C–Si bonds. WithN-tosylhydrazones as the precursors for non-stabilized diazo compound, this type of reaction becomes practically useful in organic synthesis. Transition-metal-free synthetic methodologies for borylation,gem-diborylation,gem-silylborylation arylation, 2,2,2-trifluoroethylation andgem-difluorovinylation have been successfully developed.
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22

Wu, Yuanqi, Lizuo Wu, Zhan-Ming Zhang, Bing Xu, Yu Liu, and Junliang Zhang. "Enantioselective difunctionalization of alkenes by a palladium-catalyzed Heck/borylation sequence." Chemical Science 13, no. 7 (2022): 2021–25. http://dx.doi.org/10.1039/d1sc06229h.

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A palladium catalyzed enantioselective Heck/borylation reaction of alkene-tethered aryl iodides was realized, delivering a variety of 2,3-dihydrobenzofuranyl boronic esters in high yield with excellent enantioselectivity.
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23

Yoshimura, Aya, Michiyo Yoshinaga, Hiroshi Yamashita, Masayasu Igarashi, Shigeru Shimada, and Kazuhiko Sato. "A convenient and clean synthetic method for borasiloxanes by Pd-catalysed reaction of silanols with diborons." Chemical Communications 53, no. 43 (2017): 5822–25. http://dx.doi.org/10.1039/c7cc02420g.

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24

Yang, Shengbiao, and Juntao Ye. "Borylation of azines via a Minisci-type reaction." Chem 7, no. 7 (July 2021): 1703–5. http://dx.doi.org/10.1016/j.chempr.2021.06.013.

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25

Kruppa, Marco, and Thomas J. J. Müller. "Masuda Borylation–Suzuki Coupling (MBSC) Sequence: A One-Pot Process to Access Complex (hetero)Biaryls." Catalysts 13, no. 2 (February 4, 2023): 350. http://dx.doi.org/10.3390/catal13020350.

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The direct formation of (hetero)biaryls from readily available (hetero)aryl halides under mild reaction conditions can be efficiently achieved through the Masuda borylation–Suzuki coupling (MBSC) sequence. The MBSC sequence catenates Pd-catalyzed Masuda borylation and Suzuki coupling into a one-pot process, giving access to diverse symmetrically and unsymmetrically substituted scaffolds. (Hetero)biaryls are ubiquitous structural motifs that appear in natural products, pharmaceutically relevant scaffolds, functional dyes, and several other structures. This review summarizes the development of the MBSC sequence and its improvements over the past two decades.
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26

Hale, Lillian V. A., David G. Emmerson, Emma F. Ling, Andrew J. Roering, Marissa A. Ringgold, and Timothy B. Clark. "An ortho-directed C–H borylation/Suzuki coupling sequence in the formation of biphenylbenzylic amines." Organic Chemistry Frontiers 2, no. 6 (2015): 661–64. http://dx.doi.org/10.1039/c4qo00348a.

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27

Pujol, Alba, Adam D. J. Calow, Andrei S. Batsanov, and Andrew Whiting. "One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived imines; functionalisation to homoallylic boronate carboxylate ester derivatives." Organic & Biomolecular Chemistry 13, no. 18 (2015): 5122–30. http://dx.doi.org/10.1039/c4ob02657h.

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28

Franco, Mario, Emily L. Vargas, Mariola Tortosa, and M. Belén Cid. "Coupling of thiols and aromatic halides promoted by diboron derived super electron donors." Chemical Communications 57, no. 88 (2021): 11653–56. http://dx.doi.org/10.1039/d1cc05294b.

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Diboron-based super electron donors (SEDs) efficiently catalyze the coupling between thiols and aryl halides through a SRN1 mechanism. Remarkably, under the optimized conditions, the competitive borylation reaction of the aryl halides is suppressed.
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29

Hu, Jiefeng, Matthias Ferger, Zhuangzhi Shi, and Todd B. Marder. "Recent advances in asymmetric borylation by transition metal catalysis." Chemical Society Reviews 50, no. 23 (2021): 13129–88. http://dx.doi.org/10.1039/d0cs00843e.

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We provide a comprehensive overview of transition metal-catalysed asymmetric borylation processes to construct C–B, C–C, and other C–heteroatom bonds with considerable attention devoted to the reaction modes and the mechanisms involved.
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30

Franco, Mario, Raquel Sainz, Al Mokhtar Lamsabhi, Cristina Díaz, Mariola Tortosa, and M. Belén Cid. "Evaluation of the role of graphene-based Cu(i) catalysts in borylation reactions." Catalysis Science & Technology 11, no. 10 (2021): 3501–13. http://dx.doi.org/10.1039/d1cy00104c.

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A methodical experimental and theoretical analysis of different carbon-based Cu(i) materials in the context of the development of an efficient, general, scalable, and sustainable borylation reaction of aliphatic and aromatic halides has been performed.
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31

Chen, Shuangshuang, Zhangjin Pan, and Yan Wang. "PPh3-Mediated Borylation of Arenediazonium Salts with Bis(pinacolato)diborane." Zeitschrift für Naturforschung B 69, no. 9-10 (October 1, 2014): 982–86. http://dx.doi.org/10.5560/znb.2014-4139.

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AbstractA metal-free, PPh3-mediated borylation reaction of arenediazonium salts with bis(pinacolato)diborane has been developed under mild conditions. The process provides an attractive alternative to the traditional preparation of arylboronates, albeit in moderate yields
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32

Tsurugi, Hayato, Kazushi Mashima, Luis C. Misal Castro, and Ibrahim Sultan. "Pyridine-Mediated B–B Bond Activation of (RO)2B–B(OR)2 for Generating Borylpyridine Anions and Pyridine-Stabilized Boryl Radicals as Useful Boryl Reagents in Organic Synthesis." Synthesis 53, no. 18 (April 20, 2021): 3211–26. http://dx.doi.org/10.1055/a-1486-8169.

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AbstractSignificant developments have been achieved in recent years toward the utilization of (RO)2B–B(OR)2 for exploring transition-metal-free organic transformations in organic synthesis. Among the various combinations of Lewis bases with diborons developed so far, pyridine derivatives are simple, commercially available, and cheap compounds to expand the synthetic utility of diborons by generating borylpyridine anions and pyridine-stabilized boryl radicals via B–B bond cleavage. These borylpyridine species mediate a series of transformations in both a catalytic and stoichiometric manner for C–X activation (X = halogen, CO2H, NR2) and concomitant C-borylation, hydroboryl­ation, C–C bond formation, and reduction reactions.1 Introduction2 Reaction Pathway for B–B Bond Cleavage of Diborons with Electron-Deficient Pyridines3 Pyridine-Mediated B–B Bond Activation of (RO)2B–B(OR)2 for Application in Organic Synthesis3.1 Dehalogenative C-Borylation3.2 Desulfonative C-Borylation3.3 Decarboxylative C-Borylation3.4 Deaminative C-Borylation3.5 Hydroborylation3.6 C–C Bond Formation3.7 Pyridine Functionalization3.8 Deoxygenation and N-Borylation Reactions4 Conclusions
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33

Yao, Zhengjie, Zhenwei Zhang, Jiali Li, Ji Jia, Si Ma, Yongfeng Zhi, Hong Xia, and Xiaoming Liu. "Fully π-conjugated, diyne-linked covalent organic frameworks formed via alkyne–alkyne cross-coupling reaction." Materials Chemistry Frontiers 6, no. 4 (2022): 466–72. http://dx.doi.org/10.1039/d1qm01322j.

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A diyne-linked COF was synthesized by palladium catalyzed alkyne–alkyne coupling for the first time, and it exhibited excellent heterogeneous photocatalytic performances in metal-free borylation of arylamines.
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34

Van Hoveln, R. J., S. C. Schmid, M. Tretbar, C. T. Buttke, and J. M. Schomaker. "Formal asymmetric hydrobromination of styrenes via copper-catalyzed 1,3-halogen migration." Chem. Sci. 5, no. 12 (2014): 4763–67. http://dx.doi.org/10.1039/c4sc02040e.

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An enantioselective Cu(i)-catalyzed 1,3-halogen migration reaction accomplishes a formal hydrobromination by transferring a bromine activating group from a sp2 carbon to a benzylic carbon in good er and with concomitant borylation of the Ar–Br bond.
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35

Toyota, Kozo, Shinichi Mikami, Akihiro Matsuo, and Eunsang Kwon. "Synthesis of 4,7′-Bibenzo[b]thiophenes Bearing Several Different Substituents at 2-, 2′-, 4′-, and 7-Positions; Structurally Featured Molecular Scaffolds for Selective Substitution." Synlett 32, no. 18 (September 28, 2021): 1826–32. http://dx.doi.org/10.1055/s-0040-1719839.

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AbstractFour isomers of 4,7′-bibenzothiophene scaffolds bearing two different halogen (Br, Cl) and triisopropylsilyl substituents have been synthesized from the two multihalobenzo[b]thiophenes via iodoselective Miyaura borylation reaction using potassium benzoate as a base. Further investigation into the reactivity of 4,7′-bibenzothiophenes in substitution reaction, Suzuki–Miyaura cross-coupling reaction, and C–H direct arylation reaction revealed that tetrasubstituted 4,7′-bibenzothiophenes can be synthesized site- (chemo-) selectively, which are promising novel components for molecular architecture.
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36

Zhang, Yahui, Xiangyu Zhao, Ce Bi, Wenqi Lu, Mengyuan Song, Dongdong Wang, and Guangyan Qing. "Selective electrocatalytic hydroboration of aryl alkenes." Green Chemistry 23, no. 4 (2021): 1691–99. http://dx.doi.org/10.1039/d0gc03890c.

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A CH3CN-involved electrochemical mono- or di-functional borylation reaction with alkenes and HBpin as substrates was reported. Functional group transformation and gram-scale synthesis demonstrated the utility of this method and showed great potential application.
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37

Huang, Genping, Marcin Kalek, Rong-Zhen Liao, and Fahmi Himo. "Mechanism, reactivity, and selectivity of the iridium-catalyzed C(sp3)–H borylation of chlorosilanes." Chemical Science 6, no. 3 (2015): 1735–46. http://dx.doi.org/10.1039/c4sc01592d.

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DFT calculations are used to elucidate the reaction mechanism, the role of the chlorosilyl group, and primary vs. secondary and C(sp3)–H vs. C(sp2)–H selectivity of the iridium-catalyzed borylation of chlorosilanes.
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38

Zhou, Xin-Feng, Ya-Dong Wu, Jian-Jun Dai, Yong-Jia Li, Yu Huang, and Hua-Jian Xu. "Borylation of primary and secondary alkyl bromides catalyzed by Cu2O nanoparticles." RSC Advances 5, no. 58 (2015): 46672–76. http://dx.doi.org/10.1039/c5ra06631j.

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A Cu2O nanoparticle catalyzed borylation of alkylboronic esters is developed, with mild reaction conditions, high yield and in the absence of ligands which otherwise are essential in homogenous catalysis, using bis(pinacolato)diboron as the boron source.
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39

Rueping, Magnus, Shao-Chi Lee, Lin Guo, Huifeng Yue, and Hsuan-Hung Liao. "Nickel-Catalyzed Decarbonylative Silylation, Borylation, and Amination of Arylamides via a Deamidative Reaction Pathway." Synlett 28, no. 19 (October 23, 2017): 2594–98. http://dx.doi.org/10.1055/s-0036-1591495.

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A nickel-catalyzed decarbonylative silylation, borylation, and amination of amides has been developed. This new methodology allows the direct interconversion of amides to arylsilanes, arylboronates, and arylamines and enables a facile route for carbon–heteroatom bond formations in a straightforward and mild fashion.
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40

Hooper, A., A. Zambon, and C. J. Springer. "A novel protocol for the one-pot borylation/Suzuki reaction provides easy access to hinge-binding groups for kinase inhibitors." Organic & Biomolecular Chemistry 14, no. 3 (2016): 963–69. http://dx.doi.org/10.1039/c5ob01915j.

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41

Sole, Cristina, Amadeu Bonet, André H. M. de Vries, Johannes G. de Vries, Laurent Lefort, Henrik Gulyás, and Elena Fernández. "Influence of Phosphoramidites in Copper-Catalyzed Conjugate Borylation Reaction." Organometallics 31, no. 22 (April 26, 2012): 7855–61. http://dx.doi.org/10.1021/om300194k.

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42

Welle, Alexandre, Virginie Cirriez, and Olivier Riant. "ChemInform Abstract: Copper Catalyzed Tandem Conjugated Borylation-Aldol Reaction." ChemInform 43, no. 44 (October 4, 2012): no. http://dx.doi.org/10.1002/chin.201244055.

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43

Yang, Liting, Jinjin Ma, Xiaomin Peng, Danyang Wang, Tao Guo, Bingxin Yuan, Heng Li, Panke Zhang, and Guanyu Yang. "Rhodium-Catalyzed Borylation/Protonation Tandem Reaction of Hydroxylated Diarylethynes." Asian Journal of Organic Chemistry 6, no. 6 (April 5, 2017): 698–701. http://dx.doi.org/10.1002/ajoc.201700176.

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44

Gupta, Shiv S., Krishna K. Sharma, Manoj Prajapati, Gajanan K. Rathod, and Rahul Jain. "Synthesis of Biquinolines via a Pd‐Catalyzed Borylation Reaction." Asian Journal of Organic Chemistry 9, no. 10 (September 6, 2020): 1581–84. http://dx.doi.org/10.1002/ajoc.202000356.

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45

Vogels, Christopher M., Paul E. O'Connor, Trevor E. Phillips, Keith J. Watson, Michael P. Shaver, Paul G. Hayes, and Stephen A. Westcott. "Rhodium-catalyzed hydroborations of allylamine and allylimines1." Canadian Journal of Chemistry 79, no. 12 (December 1, 2001): 1898–905. http://dx.doi.org/10.1139/v01-177.

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The in situ rhodium-catalyzed addition of catecholborane (HBcat, cat = 1,2-O2C6H4) and pinacolborane (HBpin, pin = 1,2-O2C2Me4) to allylamine, allylimine, 2- and 4-vinylpyridines, and a thienyl imine has been examined using multinuclear NMR spectroscopy. Although reactions of allylamine (H2NCH2CH=CH2) and HBcat gave complex product distributions arising from competing dehydrogenative borylation pathways, addition of HBpin to allylamine using a rhodium catalyst afforded only products arising from hydroboration (RN(Bpin)CH2CH2CH2Bpin, where R = H, Bpin) and hydrogenation (RN(Bpin)CH2CH2CH3). Hydroboration of allylimines (RHC=NCH2CH=CH2, R = Ar) with HBcat occurs initially at the more reactive imine functionality to give unsaturated borylamines (RCH2N(Bcat)CH2CH=CH2). Further reaction with HBcat gives varying amounts of hydroboration products RCH2N(Bcat)CH2CH2CH2Bcat and RCH2N(Bcat)CH2CH(Bcat)CH3 as well as the diboration product RCH2N(Bcat)CH2CH2CH(Bcat)2, depending on the choice of catalyst. Reactions with related unsaturated pyridine derivatives are complicated by extensive degradation, which can be avoided by coordination of the pyridine nitrogen to a Lewis acid. The first examples of metal-catalyzed hydroboration of imines using HBpin are also reported.Key words: catalysis, hydroboration, boronate esters, dehydrogenative borylation, allylimines.
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46

Zhu, Jianan, Ying Wei, Dongqing Lin, Changjin Ou, Linghai Xie, Yu Zhao, and Wei Huang. "One-pot synthesis of benzoxaborole derivatives from the palladium-catalyzed cross-coupling reaction of alkoxydiboron with unprotected o-bromobenzylalcohols." Organic & Biomolecular Chemistry 13, no. 46 (2015): 11362–68. http://dx.doi.org/10.1039/c5ob01781e.

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Under very mild conditions, functionalized benzoxaborole derivatives were prepared in good to excellent yields via a palladium-catalyzed Miyaura borylation reaction of readily available unprotected o-bromobenzylalcohols, and bis(pinacolato)diboron (B2pin2) without the assistance of an acid.
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47

Ito, Hajime, Eiji Yamamoto, Satoshi Maeda, and Tetsuya Taketsugu. "Transition-Metal-Free Boryl Substitution Using Silylboranes and Alkoxy Bases." Synlett 28, no. 11 (April 26, 2017): 1258–67. http://dx.doi.org/10.1055/s-0036-1588772.

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Silylboranes are used as borylation reagents for organohalides in the presence of alkoxy bases without transition-metal catalysts. PhMe2Si–B(pin) reacts with a variety of aryl, alkenyl, and alkyl halides, including sterically hindered examples, to provide the corresponding organoboronates in good yields with high borylation/silylation ratios, showing good functional group compatibility. Halogenophilic attack of a silyl nucleophile on organohalides, and subsequent nucleophilic attack on the boron electrophile are identified to be crucial, based on the results of extensive theoretical and experimental studies. This boryl­ation reaction is further applied to the first direct dimesitylboryl (BMes2) substitution of aryl halides using Ph2MeSi–BMes2 and Na(O-t-Bu), affording aryldimesitylboranes, which are regarded as an important class of compounds for organic materials.1 Introduction2 Boryl Substitution of Organohalides with PhMe2Si–B(pin)/Alkoxy Bases3 Mechanistic Investigations4 DFT Mechanistic Studies Using an Artificial Force Induced Reaction (AFIR) Method5 Dimesitylboryl Substitution of Aryl Halides with Ph2MeSi–BMes2/Na(O-t-Bu)6 Conclusion
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48

Pandarus, Valerica, Geneviève Gingras, François Béland, Rosaria Ciriminna, and Mario Pagliaro. "Clean and fast cross-coupling of aryl halides in one-pot." Beilstein Journal of Organic Chemistry 10 (April 22, 2014): 897–901. http://dx.doi.org/10.3762/bjoc.10.87.

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Unsymmetrically coupled biaryls are synthesized in high yield starting from different aryl bromides and bis(pinacolato)diboron by carrying out the Miyaura borylation reaction followed by the Suzuki–Miyaura reaction in the same reaction pot over 1–2 mol % SiliaCat DPP-Pd. The SiliaCat DPP-Pd catalyst is air-stable and the method does not require the use of inert conditions. The use of non-toxic isopropanol or 2-butanol as reaction solvent further adds to the environmental benefits of this new green synthetic methodology.
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49

Nhari, Laila M., Elham N. Bifari, Aisha R. Al-Marhabi, Huda A. Al-Ghamdi, Sameera N. Al-Ghamdi, Fatimah A. M. Al-Zahrani, Khalid O. Al-Footy, and Reda M. El-Shishtawy. "Synthesis of Novel Key Chromophoric Intermediates via C-C Coupling Reactions." Catalysts 12, no. 10 (October 21, 2022): 1292. http://dx.doi.org/10.3390/catal12101292.

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The fundamentals of Pd-catalyzed Csp2−Csp2 Miyaura borylation, Suzuki cross-coupling, and Stille cross-coupling reactions for a variety of borylated precursors based on phenothiazine (PTZ), phenoxazine (POZ), carbazole (Cz), and quinoxaline (QX) units have been explored. Three palladium-based catalysts were chosen for this study: Pd(PPh3)4, Pd(PPh3)2Cl2, and Pd(dppf)Cl2, applying different reaction conditions. Around 16 desired chromophores were successfully designed and synthesized using C-C cross-coupling reactions in moderate to excellent yields, including PTZ, POZ, and Cz units coupled with QX, indolinium iodide, thienyl, phenyl, or triphenylamine moieties. Additionally, PTZ, POZ, and Cz have been employed in synthesizing various pinacol boronate ester derivatives in good to moderate yields. Interestingly, Pd(dppf)Cl2 was found to be the best catalyst for borylation, and C-C cross-coupling reactions occurred in as little as 30 min, with an excellent yield exceeding 98%. Pd(PPh3)4 and Pd(PPh3)2Cl2 catalyzed the reaction to obtain the desired products in moderate to good yields after a long time (20–24 h). On the other hand, the Suzuki-Miyaura cross-coupling between N-(2-methyl)hexyl carbazole pinacol boronate ester derivative 10c and three halogenated quinoxaline derivatives—4-(3-(5-bromothiophen-2-yl)quinoxalin-2-yl)benzaldehyde (27), 4-(5-(3-(5-bromothiophen-2-yl)quinoxalin-2-yl)thiophen-2-yl)benzaldehyde (30), and 4-(3-chloroquinoxalin-2-yl)benzaldehyde (25) catalyzed by Pd(PPh3)4—afforded three carbazole-quinoxaline chromophores (28, 30, and 31, respectively) in 2–3 h, with good to excellent yields reaching 86%. The electron-deficient QX couplers proved to be coupled efficiently using the Stille coupling reaction, which involves the coupling between electron-rich orgaostannane and electron-deficient halide. The synthesized precursors and desired chromophores were characterized by FTIR, 1H-NMR, 13C-NMR, and HRMS.
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50

Coffinet, Anaïs, Dan Zhang, Laure Vendier, Sébastien Bontemps, and Antoine Simonneau. "Borane-catalysed dinitrogen borylation by 1,3-B–H bond addition." Dalton Transactions 50, no. 16 (2021): 5582–89. http://dx.doi.org/10.1039/d1dt00317h.

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1,3-B–H addition of various boranes over a W–NN motif has been explored to probe its scope and limitations as a method for N2 borylation. The reaction can be catalysed or not, and boranes that undergo retrohydroboration react as monoalkylboranes.
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