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Selective Synthesis of Z-Silyl Enol Ethers via Ni-Catalyzed Remote Functionalization of Ketones

Sinem Guven, Gourab Kundu, Andrea Weßels, Jas S. Ward, Kari Rissanen and Franziska Schoenebeck*

*Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Email: franziska.schoenebeckrwth-aachen.de

S. Guven, G. Kundu, A. Wessels, J. S. Ward, K. Rissanen, F. Schoenebeck, J. Am. Chem. Soc., 2021, 143, 8375-8380.

DOI: 10.1021/jacs.1c01797


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Abstract

A remote functionalization strategy enables a Z-selective synthesis of silyl enol ethers of (hetero)aromatic and aliphatic ketones via Ni-catalyzed chain walking from a distant olefin site. Mechanistic data indicate that a Ni(I) dimer is formed under these conditions, which serves as a catalyst resting state and, upon reaction with an alkyl bromide, is converted to [Ni(II)-H] as active catalyst.

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proposed mechanism



Key Words

Silyl Enol Ethers, Manganese


ID: J48-Y2021