Solvent-Dependent Change in the Rate-Determining Step of Au(I)-Catalyzed -Propargyl Benzamide Cyclization.

J Org Chem

Department of Chemistry, Wake Forest University, 1834 Wake Forest Road, Winston-Salem, North Carolina 27109, United States.

Published: August 2025


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Article Abstract

The cyclization of -propargyl benzamide with gold catalysts has become a popular benchmark reaction over the past two decades. The prevailing consensus denotes protodeauration as rate-limiting. Cyclization with [Au(NCCH)]SbF and AuOTs ( = -Bu(-biphenyl)P, also known as Johnphos) in dichloromethane and methanol in conjunction with deuterium labeling studies reveals a solvent-dependent switch to π-activation for the rate-limiting step. Computational calculations support this change of the rate-determining step.

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http://dx.doi.org/10.1021/acs.joc.5c00787DOI Listing

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