Synlett 2016; 27(08): 1139-1144
DOI: 10.1055/s-0035-1561351
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© Georg Thieme Verlag Stuttgart · New York

Radical-Mediated Ring-Opening Functionalization of Cyclobutanols: A Shortcut to γ-Substituted Ketones

Rongguo Ren
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, P. R. of China
,
Chen Zhu*
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, P. R. of China
b  Key Laboratory of Synthesis Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032, P. R. of China   Email: chzhu@suda.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 16 December 2015

Accepted after revision: 06 January 2016

Publication Date:
04 February 2016 (online)

Dedicated to Professor Guo-Qiang Lin

Abstract

Cyclobutanols serve as privileged precursors for the preparation of γ-substituted ketones. We highlight recent advances in the radical-mediated ring-opening functionalization of cyclobutanols by fluorination, chlorination, bromination, or azidation, which open up a new vista for the synthesis of ketone derivatives.

1 Introduction

2 Silver-Catalyzed Fluorination, Chlorination, and Bromination of Cyclobutanols

3 Manganese-Catalyzed Azidation of Cyclobutanols

4 Conclusion

 
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