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Fragment Couplings via CO2 Extrusion-Recombination: Expansion of a Classic Bond-Forming Strategy via Metallaphotoredox

Chi "Chip" Le and David W. C. MacMillan*

*Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States, Email: dmacmillprinceton.edu

C. Le, D. W. C. MacMillan, J. Am. Chem. Soc., 2015, 137, 11938-11941.

DOI: 10.1021/jacs.5b08304 (free Supporting Information)


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Abstract

A wide variety of mixed anhydrides formed in situ from carboxylic acids and acyl chlorides can subsequently undergo metal insertion-decarboxylation-recombination to provide ketones in very good yield when subjected to metallaphotoredox catalysis. A three-step synthesis of the medicinal agent edivoxetine is also described.

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Key Words

pyrrolidines


ID: J48-Y2015