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Journal articles on the topic 'Allylic halogenation'

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Published: 6 September 2023

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1

Pal, Rita, Anupama Das, and Narayanaswamy Jayaraman. "One-pot oligosaccharide synthesis: latent-active method of glycosylations and radical halogenation activation of allyl glycosides." Pure and Applied Chemistry 91, no. 9 (September 25, 2019): 1451–70. http://dx.doi.org/10.1515/pac-2019-0306.

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Abstract Chemical glycosylations occupy a central importance to synthesize tailor-made oligo- and polysaccharides of functional importance. Generation of the oxocarbenium ion or the glycosyl cation is the method of choice in order to form the glycosidic bond interconnecting a glycosyl moiety with a glycosyl/aglycosyl moiety. A number of elegant methods have been devised that allow the glycosyl cation formation in a fairly stream-lined manner to a large extent. The latent-active method provides a powerful approach in the protecting group controlled glycosylations. In this context, allyl glycosides have been developed to meet the requirement of latent-active reactivities under appropriate glycosylation conditions. Radical halogenation provides a newer route of activation of allyl glycosides to an activated allylic glycoside. Such an allylic halide activation subjects the glycoside reactive under acid catalysis, leading to the conversion to a glycosyl cation and subsequent glycosylation with a number of acceptors. The complete anomeric selectivity favoring the 1,2-trans-anomeric glycosides points to the possibility of a preferred conformation of the glycosyl cation. This article discusses about advancements in the selectivity of glycosylations, followed by delineating the allylic halogenation of allyl glycoside as a glycosylation method and demonstrates synthesis of a repertoire of di- and trisaccharides, including xylosides, with varied protecting groups.
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2

Das, Anupama, and Narayanaswamy Jayaraman. "Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides." Organic & Biomolecular Chemistry 19, no. 42 (2021): 9318–25. http://dx.doi.org/10.1039/d1ob01298c.

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A one-pot CCl4-free allylic halide activation of allyl glycosides, followed by glycosylation with acceptors, is conducted in a latent-active manner. PhCF3 as the solvent and TMSOTf/Tf2O as the promoter system are optimal for the reaction.
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3

Chen, Chao, Jun-Chen Kang, Chen Mao, Jia-Wei Dong, Yu-Yang Xie, Tong-Mei Ding, Yong-Qiang Tu, Zhi-Min Chen, and Shu-Yu Zhang. "Electrochemical halogenation/semi-pinacol rearrangement of allylic alcohols using inorganic halide salt: an eco-friendly route to the synthesis of β-halocarbonyls." Green Chemistry 21, no. 15 (2019): 4014–19. http://dx.doi.org/10.1039/c9gc01152h.

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4

Easton, Christopher J., Alison J. Edwards, Stephen B. McNabb, Martin C. Merrett, Jenny L. O'Connell, Gregory W. Simpson, Jamie S. Simpson, and Anthony C. Willis. "Allylic halogenation of unsaturated amino acids." Org. Biomol. Chem. 1, no. 14 (2003): 2492–98. http://dx.doi.org/10.1039/b303719c.

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5

Yin, Jiandong, Christina E. Gallis, and John D. Chisholm. "Tandem Oxidation/Halogenation of Aryl Allylic Alcohols under Moffatt−Swern Conditions." Journal of Organic Chemistry 72, no. 18 (August 2007): 7054–57. http://dx.doi.org/10.1021/jo0711992.

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6

Hanson, James R., Peter B. Hitchcock, Paul B. Reese, and Almaz Truneh. "Steroidal allylic and homoallylic rearrangements during halogenation with triphenylphosphine and carbon tetrachloride." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1988): 1469. http://dx.doi.org/10.1039/p19880001469.

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7

Liu, Na, Casi M. Schienebeck, Michelle D. Collier, and Weiping Tang. "Effect of halogenation reagents on halocyclization and Overman rearrangement of allylic trichloroacetimidates." Tetrahedron Letters 52, no. 47 (November 2011): 6217–19. http://dx.doi.org/10.1016/j.tetlet.2011.09.057.

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8

Bandgar, Babasaheb P., and Sampada V. Bettigeri. "Efficient and Selective Halogenation of Allylic and Benzylic Alcohols under Mild Conditions." Monatshefte f�r Chemie/Chemical Monthly 135, no. 10 (August 13, 2004): 1251–55. http://dx.doi.org/10.1007/s00706-004-0212-8.

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9

Hamashima, Yoshitaka, and Yuji Kawato. "Enantioselective Bromocyclization of Allylic Amides Mediated by Phosphorus Catalysis." Synlett 29, no. 10 (May 14, 2018): 1257–71. http://dx.doi.org/10.1055/s-0036-1591579.

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Halocyclization of alkenes is commonly employed to increase molecular complexity during organic synthesis because it enables double installation of heteroatoms on a carbon–carbon double bond. Moreover, stereodefined halogenated compounds are widely found among naturally occurring compounds and can serve as versatile chiral building blocks. Therefore, the development of asymmetric halocyclization reactions is of great interest and, in recent years, there has been remarkable progress in catalytic asymmetric halogenation reactions. This account summarizes recent progress made by our group on phosphorus-­catalyzed enantioselective bromocyclization of allylic amides. Building on a comprehensive study of the reaction mechanism, we discovered an intriguing catalytic reaction in which P+Br species serves as a fine-tuning element for substrate fixation. We also describe the application of this bromocyclization to asymmetric desymmetrization of 1,4-diene substrates and a concise synthesis of the HIV-protease inhibitor ­nelfinavir using the newly developed desymmetrization reaction as a key step.1 Introduction2 Enantioselective Bromocyclization of Allylic Amides with a BINAP Catalyst2.1 Bromocyclization with a P/P Catalyst2.2 Bromocyclization with a P/P=O Catalyst3 Desymmetrization of Bisallylic Amides through Enantioselective Bromocyclization3.1 Desymmetrization of Bisallylic Amides3.2 Enantioselective Synthesis of Nelfinavir4 Summary
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10

Liu, Na, Casi M. Schienebeck, Michelle D. Collier, and Weiping Tang. "ChemInform Abstract: Effect of Halogenation Reagents on Halocyclization and Overman Rearrangement of Allylic Trichloroacetimidates." ChemInform 43, no. 9 (February 2, 2012): no. http://dx.doi.org/10.1002/chin.201209054.

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11

Aghahosseini, Hamideh, Ali Ramazani, Farideh Gouranlou, and Sang Woo Joo. "Nanoreactors Technology in Green Organic Synthesis." Current Organic Synthesis 14, no. 6 (September 28, 2017): 810–64. http://dx.doi.org/10.2174/1570179413666161008200641.

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Background: Nanoreactors technology represents a promising tool for efficient and selective organic synthesis typically under “green” and sustainable reaction conditions. These structures with generating a confined reaction environment to accommodate that both reactants and catalysts can change the reaction pathways and induce new activities and selectivities. Objective: The paper reviews literature examples in which nanoreactors were employed in various types of organic and metal catalyzed reactions including multicomponent reactions, palladium-catalyzed coupling reactions, olefin metathesis, aza-Cope rearrangement, allylic alcohol isomerization, cyclization reactions, ring opening reactions, halogenation reactions, hydrolysis reactions, hydroformylation reactions, cascade reactions, addition reactions, oxidation reactions and reduction reactions. The reactions' survey is accompanied with the explanation of structure and performance of nanoreactors that are applied there. Conclusion: The availability of comprehensive information about the role of nanoreactors technology in green organic synthesis and investigation of different aspects of them such as their structures, mechanisms and synthetic utility can assist researchers in designing the greener approaches in organic synthesis.
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12

Zeng, Zhixuan, Xudong Xun, Liwu Huang, Jiecheng Xu, Gongming Zhu, Guofeng Li, Wangsheng Sun, Liang Hong, and Rui Wang. "Catalyst-free tandem halogenation/semipinacol rearrangement of allyl alcohols with sodium halide in water." Green Chemistry 20, no. 11 (2018): 2477–80. http://dx.doi.org/10.1039/c8gc00478a.

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13

Pal, Rita, Anupama Das, and Narayanaswamy Jayaraman. "Radical halogenation-mediated latent–active glycosylations of allyl glycosides." Chemical Communications 54, no. 6 (2018): 588–90. http://dx.doi.org/10.1039/c7cc07332a.

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Radical halogenation-mediated glycosylation using allyl glycosides as donors and as acceptors emerges to be an efficient and hither-to unknown glycosylation method, adhering to the concept of the latent–active methodology.
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14

Stamm, Reiner, and Henning Hopf. "Polar reactions of acyclic conjugated bisallenes." Beilstein Journal of Organic Chemistry 9 (January 8, 2013): 36–48. http://dx.doi.org/10.3762/bjoc.9.5.

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The chemical behaviour of various alkyl-substituted, acyclic conjugated bisallenes in reactions involving polar intermediates and/or transition states has been investigated on a broad scale for the first time. The reactions studied include lithiation, reaction of the thus formed organolithium salts with various electrophiles (among others, allyl bromide, DMF and acetone), oxidation to cyclopentenones and epoxides, hydrohalogenation (HCl, HBr addition), halogenation (Br2 and I2 addition), and [2 + 2] cycloaddition with chlorosulfonyl isocyanate. The resulting adducts were fully characterized by spectroscopic and analytical methods; they constitute interesting substrates for further organic transformations.
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15

Beeson, Teresa D., Anthony Mastracchio, Jun-Bae Hong, Kate Ashton, and David W. C. MacMillan. "Enantioselective Organocatalysis Using SOMO Activation." Science 316, no. 5824 (April 27, 2007): 582–85. http://dx.doi.org/10.1126/science.1142696.

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The asymmetric α-addition of relatively nonpolar hydrocarbon substrates, such as allyl and aryl groups, to aldehydes and ketones remains a largely unsolved problem in organic synthesis, despite the wide potential utility of direct routes to such products. We reasoned that well-established chiral amine catalysis, which activates aldehydes toward electrophile addition by enamine formation, could be expanded to this important reaction class by applying a single-electron oxidant to create a transient radical species from the enamine. We demonstrated the concept of singly occupied molecular orbital (SOMO) activation with a highly selective α-allylation of aldehydes, and we here present preliminary results for enantioselective heteroarylations and cyclization/halogenation cascades.
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16

Benmaarouf-khallaayoun, Z., M. Baboulene, V. Speziale, and Lattes. "HYDROBORATION OF UNSATURATED AMINES X. HYDROBORATION-HALOGENATION OF ALLYL PHOSPHORAMIDATES ROUTE TO γ-HALOGENOPROPYL PHOSPHORAMIDATES AND γ-HALOGENATED AMINES." Phosphorous and Sulfur and the Related Elements 36, no. 3-4 (April 1988): 181–87. http://dx.doi.org/10.1080/03086648808079015.

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17

Yamanaka, Masamichi, Mitsuhiro Arisawa, Atsushi Nishida, and Masako Nakagawa. "An intriguing effect of Yb(OTf)3–TMSCl in the halogenation of 1,1-disubstituted alkenes by NXS: selective synthesis of allyl halides." Tetrahedron Letters 43, no. 13 (March 2002): 2403–6. http://dx.doi.org/10.1016/s0040-4039(02)00260-5.

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18

Yamanaka, Masamichi, Mitsuhiro Arisawa, Atsushi Nishida, and Masako Nakagawa. "ChemInform Abstract: An Intriguing Effect of Yb(OTf)3-TMSCl in the Halogenation of 1,1-Disubstituted Alkenes by NXS: Selective Synthesis of Allyl Halides." ChemInform 33, no. 29 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200229068.

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19

Bandgar, Babasaheb P., and Sampada V. Bettigeri. "Efficient and Selective Halogenation of Allylic and Benzylic Alcohols under Mild Conditions." ChemInform 36, no. 5 (February 1, 2005). http://dx.doi.org/10.1002/chin.200505068.

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20

Yin, Jiandong, Christina E. Gallis, and John D. Chisholm. "ChemInform Abstract: Tandem Oxidation/Halogenation of Aryl Allylic Alcohols under Moffatt—Swern Conditions." ChemInform 39, no. 2 (January 8, 2008). http://dx.doi.org/10.1002/chin.200802074.

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21

HANSON, J. R., P. B. HITCHCOCK, P. B. REESE, and A. TRUNEH. "ChemInform Abstract: Steroidal Allylic and Homoallylic Rearrangements During Halogenation with Triphenylphosphine and Carbon Tetrachloride." ChemInform 19, no. 40 (October 4, 1988). http://dx.doi.org/10.1002/chin.198840257.

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22

Povidaichyk, М., М. М. Kut, S. Mykhaylychenko, M. Onysko, Yu Shermolovich, and V. Lendel. "ARYLTELLUROCHLORINATION OF N-ALLYLTHIOAMIDE OF TRIFLUOROACETIC ACID." Scientific Bulletin of the Uzhhorod University. Series «Chemistry» 45, no. 1 (June 30, 2021). http://dx.doi.org/10.24144/2414-0260.2021.1.95-98.

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Telluroganic compounds have a pronounced biological activity, namely, show antitumor, antioxidant, antiparasitic activity. The introduction of a trifluoromethyl group to such compounds can significantly increase the activity. Therefore, the aim of this study is the synthesis of tellurium-containing compounds by the electrophilic action of aryltellurium trichloride on N-allylthioamide of trifluoroacetic acid. As the object of the study of the aryltellurohalogenation process of N-allyl thioamide of trifluoroacetic acid was chosen. The selection is dictated by the presence of several nucleophilic centers suitable for the attack by electrophiles and can form both addition and cyclization products. The synthesis of the amide was performed through the interaction of ethyl ester of trifluoroacetic acid with allylamine in tetrahydrofuran followed by the treatment of the formed N-allylamide with phosphorus (V) sulfide in the presence of hexamethyldisiloxane in toluene. Propargyl trifluoroacetic acid amide was investigated in the halogenation reaction, which resulted in the addition product. It was important to establish the effect of the nature of the unsaturated alkenyl/alkynyl substituent, the additional nucleophilic center and the electrophilic reagent on the reaction pathway. The reaction of N-allyltrifluorothioacetamide with p-methoxyphenyltellurium trichloride was performed in chloroform or tetrahydrofuran at room temperature in equimolar amounts of reagents. The addition product N-(2-chloro-3- (dichloro (4-methoxyphenyl) -)-l4-4-tellanyl)propyl] -2,2,2-trifluoroethanethioamide was obtained. Similar addition products were formed in the reaction of N-allyl thioureas with aryltellurium trihalides.
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23

Shukla, Gaurav, Keshav Raghuvanshi, and Maya Shankar Singh. "Regio- and Chemoselective Access to Dihydrothiophenes and Thiophenes via Halogenation/Intramolecular C(sp2)–H Thienation of α-Allyl Dithioesters at Room Temperature." Journal of Organic Chemistry, October 7, 2022. http://dx.doi.org/10.1021/acs.joc.2c01617.

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