Issue 3, 2017

Ring-opening selenation of cyclobutanols: synthesis of γ-selenylated alkyl ketones through C–C bond cleavage

Abstract

An efficient and practical manganese-mediated ring-opening selenation of cyclobutanols is disclosed. The transformation has broad functionality tolerance, producing a variety of γ-selenylated alkyl ketones in synthetically useful yields. Mechanistically, the radical-promoted regioselective cyclic C–C bond cleavage and sp3 C–Se bond formation are involved.

Graphical abstract: Ring-opening selenation of cyclobutanols: synthesis of γ-selenylated alkyl ketones through C–C bond cleavage

Supplementary files

Article information

Article type
Research Article
Submitted
22 Nov 2016
Accepted
20 Dec 2016
First published
21 Dec 2016

Org. Chem. Front., 2017,4, 427-430

Ring-opening selenation of cyclobutanols: synthesis of γ-selenylated alkyl ketones through C–C bond cleavage

M. Wang, Z. Wu and C. Zhu, Org. Chem. Front., 2017, 4, 427 DOI: 10.1039/C6QO00744A

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