Unified Gold(I/III)-Catalyzed Arylative, Vinylative, and Alkynylative Lactonization via Iminium-Directed Cyclization
Jorge C Herrera-Luna1, Riccardo Mobili1, Cyril Ollivier1
1Institut Parisien de Chimie Moléculaire Sorbonne Université, CNRS, 4 place Jussieu, 75005 Paris, France.
Abstract:
We report a unified strategy for the synthesis of functionalized lactones via hemilabile Au(I)/Au(III) redox catalysis. Oxidative addition of aryl, vinyl, or alkynyl iodides to Au(I) is followed by iminium-directed π-activation and lactonization, using AgOTf as a halide scavenger. The method affords 49 lactones under mild, scalable conditions with broad functional group tolerance. Mechanistic studies support iminium and Au(III) intermediates. Moreover, we present a new Au(I)/(III) hemilabile complex that is particularly effective in alkynylation.
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