Chemo- and Regioselective Distal Heteroaryl ipso-Migration: A General Protocol for Heteroarylation of Unactivated Alkenes
作者： Leitao Huan , Chen Zhu , Zhen Wu , Dongping Wang , Yuan Liu
DOI: 10.1021/JACS.6B11234
关键词:
摘要: Herein we report a novel, general protocol for distal heteroaryl ipso-migration and its application to the elusive heteroarylation of unactivated alkenes. A set nitrogen-containing groups showcase migratory aptitude. This reaction provides variety fluoroalkyl functionalized heteroarenes under mild conditions. is first difunctionalization alkenes with migration.
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Zhi-Min Chen, Xiao-Ming Zhang, Yong-Qiang Tu, Radical aryl migration reactions and synthetic applications. Chemical Society Reviews. ,vol. 44, pp. 5220- 5245 ,(2015) , 10.1039/C4CS00467A
Xue-Qiang Chu, Hua Meng, You Zi, Xiao-Ping Xu, Shun-Jun Ji, Metal-free oxidative direct C(sp3)–H bond functionalization of ethers with α,α-diaryl allylic alcohols Chemical Communications. ,vol. 50, pp. 9718- 9721 ,(2014) , 10.1039/C4CC04282D
Mamoun M. Alhamadsheh, Richard A. Hudson, L. M. Viranga Tillekeratne, Design, total synthesis, and evaluation of novel open-chain epothilone analogues. Organic Letters. ,vol. 8, pp. 685- 688 ,(2006) , 10.1021/OL0528787
Xue-Qiang Chu, You Zi, Hua Meng, Xiao-Ping Xu, Shun-Jun Ji, Radical phosphinylation of α,α-diaryl allylic alcohols with concomitant 1,2-aryl migration Chemical Communications. ,vol. 50, pp. 7642- 7645 ,(2014) , 10.1039/C4CC02114B
Yu-Dong Yang, Kanji Iwamoto, Etsuko Tokunaga, Norio Shibata, Transition-metal-free oxidative trifluoromethylation of unsymmetrical biaryls with trifluoromethanesulfinate Chemical Communications. ,vol. 49, pp. 5510- 5512 ,(2013) , 10.1039/C3CC41667D
Tomislav Pintauer, Krzysztof Matyjaszewski, Atom transfer radical addition and polymerization reactions catalyzed by ppm amounts of copper complexes Chemical Society Reviews. ,vol. 37, pp. 1087- 1097 ,(2008) , 10.1039/B714578K
Hiromichi Egami, Ryo Shimizu, Yoshihiko Usui, Mikiko Sodeoka, Iron-catalyzed trifluoromethylation with concomitant C–C bond formation via 1,2-migration of an aryl group Chemical Communications. ,vol. 49, pp. 7346- 7348 ,(2013) , 10.1039/C3CC43936D
Yu-Tao He, Lian-Hua Li, Yan-Fang Yang, Zhao-Zhao Zhou, Hui-Liang Hua, Xue-Yuan Liu, Yong-Min Liang, Copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes. Organic Letters. ,vol. 16, pp. 270- 273 ,(2014) , 10.1021/OL403263C
Jincan Zhao, Hong Fang, Ruichun Song, Jie Zhou, Jianlin Han, Yi Pan, Metal-free oxidative C(sp3)–H bond functionalization of alkanes and alkylation-initiated radical 1,2-aryl migration in α,α-diaryl allylic alcohols Chemical Communications. ,vol. 51, pp. 599- 602 ,(2015) , 10.1039/C4CC07654K
Samuel Danishefsky, Paul Cain, Optically specific synthesis of estrone and 19-norsteroids from 2,6-lutidine Journal of the American Chemical Society. ,vol. 98, pp. 4975- 4983 ,(1976) , 10.1021/JA00432A044