Issue 2, 2016
From the journal:

Organic Chemistry Frontiers

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

Xuefeng Fan,‡a   Huijun Zhao,‡a   Jiajia Yu,a   Xiaoguang Bao*b  and  Chen Zhu*ac  

* Corresponding authors

a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China
E-mail: chzhu@suda.edu.cn

b College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China
E-mail: xgbao@suda.edu.cn

c Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China

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

DOI
https://doi.org/10.1039/C5QO00368G
Article type
Research Article
Submitted
11 Nov 2015
Accepted
09 Dec 2015
First published
10 Dec 2015

Org. Chem. Front., 2016,3, 227-232

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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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