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Markovnikov-Selective Radical Addition of S-Nucleophiles to Terminal Alkynes through a Photoredox Process

作者:     点击:      时间:2018-06-01

Wang, HM (Wang, Huamin)[ 1 ] ; Lu, QQ (Lu, Qingquan)[ 1 ] ; Chiang, CW (Chiang, Chien-Wei)[ 1 ] ; Luo, Y (Luo, Yi)[ 1 ] ; Zhou, JF (Zhou, Jiufu)[ 1 ] ; Wang, GY (Wang, Guangyu)[ 1 ] ; Lei, AW (Lei, Aiwen)[ 1,2 ]


ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

卷: 56

期: 2

页: 595-599

DOI: 10.1002/anie.201610000

出版年: JAN 9 2017

文献类型:Article


摘要

Direct radical additions to terminal alkynes have been widely employed in organic synthesis, providing credible access to the anti-Markovnikov products. Because of the Kharasch effect, regioselective control for the formation of Markovnikov products still remains a great challenge. Herein, we develop a transition-metal-free, visible light-mediated radical addition of S-nucleophiles toterminal alkynes, furnishing a wide array of a-substituted vinyl sulfones with exclusive Markovnikov regioselectivity. Mechanistic investigations demonstrated that radical/ radical cross-coupling might be the key step in this transformation. This radical Markovnikov addition protocol also provides an opportunity to facilitate the synthesis of other valuable a-substituted vinyl compounds.

作者信息

通讯作者地址: Lei, AW (通讯作者)

显示更多 Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China.
通讯作者地址: Lei, AW (通讯作者)
显示更多 Chinese Acad Sci, Lanzhou Inst Chem Phys, Lanzhou 730000, Peoples R China.

地址:

[ 1 ] Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China
[ 2 ] Chinese Acad Sci, Lanzhou Inst Chem Phys, Lanzhou 730000, Peoples R China

电子邮件地址:aiwenlei@whu.edu.cn


原文PDF链接:

https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201610000