Selectivity Reversal during Thia-Michael Additions Using Tetrabutylammonium Hydroxide: Operationally Simple and Extremely High Turnover

Daniel R. Nicponski*, Jennifer M. Marchi

*Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Dr., West Lafayette, IN, 47907, USA

D. R. Nicponski, J. M. Marchi, Synthesis, 2014, 46, 1725-1730.

DOI: 10.1055/s-0033-1341106

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Abstract

The use of tetrabutylammonium hydroxide as an efficient thia-Michael addition catalyst enables the conjugate addition of a broad range of mercaptan nucleophile to a very wide range of both classical and non-classical Michael acceptors. This methodology is especially attractive and operationally simple, as it generally proceeds with low catalytic loading and without excess reagent, and the produced products typically require no purification.

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Key Words

thia-Michael reaction, conjugate addition, catalysis, green chemistry

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ID: J66-Y2014