Catalytic Hydrothiolation: Counterion-Controlled Regioselectivity

Xiao-Hui Yang, Ryan T. Davison, Shao-Zhen Nie, Faben A. Cruz, Tristan M. McGinnis, Vy M. Dong*

*Department of Chemistry, University of California, Irvine, California 92697, United States, Email: dongvuci.edu

X.-H. Yang, R. T. Davison, S.-Z. Nie, F. A. Cruz, T. M. McGinnis, V. M. Dong, J. Am. Chem. Soc., 2019, 141, 3006-3013.

DOI: 10.1021/jacs.8b11395

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Abstract

The Rh-catalyzed hydrothiolation of 1,3-dienes affords either allylic or homoallylic sulfides. Regioselectivity is dictated by the choice of counterion associated with the Rh center. Coordinating counterions, such as Cl^-, favor neutral Rh complexes in which the diene binds η² to afford homoallylic sulfides.

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Catalytic Hydrothiolation: Regio- and Enantioselective Coupling of Thiols and Dienes

X.-H. Yang, R. T. Davison, V. M. Dong, J. Am. Chem. Soc., 2018, 140, 10443-10446.

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Key Words

sulfides

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ID: J48-Y2019