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