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Issue 2, 2016
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Regiospecific synthesis of distally chlorinated ketones via C–C bond cleavage of cycloalkanols

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Abstract

A variety of distally Csp3-chlorinated ketones are synthesized with good regioselectivities via silver-catalyzed ring opening of cycloalkanols under mild reaction conditions. The reaction uses only routine, inexpensive reagents and can be scaled up to gram quantities. A novel radical-mediated C–C bond cleavage/C–Cl bond formation is proposed.

Graphical abstract: Regiospecific synthesis of distally chlorinated ketones via C–C bond cleavage of cycloalkanols

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Article information


Submitted
11 Nov 2015
Accepted
09 Dec 2015
First published
10 Dec 2015

Org. Chem. Front., 2016,3, 227-232
Article type
Research Article

Regiospecific synthesis of distally chlorinated ketones via C–C bond cleavage of cycloalkanols

X. Fan, H. Zhao, J. Yu, X. Bao and C. Zhu, Org. Chem. Front., 2016, 3, 227
DOI: 10.1039/C5QO00368G

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