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

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• 作者：Huamin Wang ; Dr. Qingquan Lu ; Chien-Wei Chiang ; Yi Luo ; Jiufu Zhou ; Guangyu Wang and Prof. Aiwen Lei
• 刊名：Angewandte Chemie
• 出版年：2017
• 出版时间：January 9, 2017
• 年：2017
• 卷：129
• 期：2
• 页码：610-614
• 全文大小：1225K
• ISSN：1521-3757

文摘

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 to terminal alkynes, furnishing a wide array of α-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 α-substituted vinyl compounds.