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 ]}

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.

作者关键词:Markovnikov selectivity; photoredox catalysis; radical addition; radical cross coupling; transition-metal-free synthesis

KeyWords Plus:VINYL SULFONES; ORGANIC-SYNTHESIS; BOND FORMATION; METAL-FREE; C-S; CATALYSIS; ARYL; ALKENES; ACIDS; FUNCTIONALIZATION

通讯作者地址: Lei, AW (通讯作者)

Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China.

Chinese Acad Sci, Lanzhou Inst Chem Phys, Lanzhou 730000, Peoples R China.

地址:

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