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Issue 3, 2017
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Ring-opening selenation of cyclobutanols: synthesis of γ-selenylated alkyl ketones through C–C bond cleavage

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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

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Article information


Submitted
22 Nov 2016
Accepted
20 Dec 2016
First published
21 Dec 2016

Org. Chem. Front., 2017,4, 427-430
Article type
Research Article

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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