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

Jinyang Chen, Sihai Chen, Xinhua Xu*, Zhi Tang, Chak-Tong Au and Renhua Qiu*

*College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, People’s Republic of China, Email: xhx1581hnu.edu.cn, renhuaqiuhnu.edu.cn

J. Chen, S. Chen, X. Xu, Z. Tang, C.-T. Au, R. Qiu, J. Org. Chem., 2016, 81, 3246-3255.

DOI: 10.1021/acs.joc.6b00203 (free Supporting Information)


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Abstract

A highly regio- and stereoselective coupling of (Z)-1,2-bis(aryl(alkyl)thio)alkenes and Grignard reagents in the presence of a Ni catalyst under mild conditions enables an efficient route for the synthesis of (Z)-vinylic sulfides. (Z)-vinylic sulfides are important intermediates in the synthesis of tri- and tetrasubstituted alkenes.

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Key Words

olefination (arenes, alkanes), vinyl sulfides


ID: J42-Y2016