Nickel-Catalyzed Regioselective Cleavage of Csp2–S Bonds: Method for the Synthesis of Tri- and Tetrasubstituted Alkenes

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• 作者：Jinyang Chen ; Sihai Chen ; Xinhua Xu ; Zhi Tang ; Chak-Tong Au ; Renhua Qiu
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：81
• 期：8
• 页码：3246-3255
• 全文大小：621K
• 年卷期：0
• ISSN：1520-6904

文摘

We describe here an efficient route for the synthesis of (Z)-vinylic sulfides 3 via the highly regio- and stereoselective coupling of (Z)-1,2-bis(aryl(alkyl)thio)alkenes and Grignard reagents over a Ni catalyst under mild conditions. (Z)-Vinylic sulfides 3 are important intermediates in the synthesis of tri- and tetrasubstituted alkenes that are important construction blocks for drugs and natural products. The directing organosulfur groups (SR) can be converted to diaryl(alkyl) disulfides (RSSR) using H₂O₂ as oxidant, hence avoiding the waste of sulfur resources. The protocol provides a general method that is highly regio- and stereoselective for the synthesis of a diversity of tri- and tetrasubstituted alkenes.