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Synthesis 2017; 49(15): 3357-3365
DOI: 10.1055/s-0036-1588458
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Cyclic Diacyl Peroxides: Reactivity and Selectivity Enhancement Brought by the Cyclic Structure

Rong Zhao
b   MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, P. R. of China
c   Shenzhen Graduate School, Harbin Institute of Technology, Shenzhen 518055, P. R. of China   Email: lshi@hit.edu.cn
,
Denghu Chang
b   MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, P. R. of China
c   Shenzhen Graduate School, Harbin Institute of Technology, Shenzhen 518055, P. R. of China   Email: lshi@hit.edu.cn
,
Lei Shi  *
a   Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, Jingmen 448000, P. R. of China
b   MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, P. R. of China
c   Shenzhen Graduate School, Harbin Institute of Technology, Shenzhen 518055, P. R. of China   Email: lshi@hit.edu.cn
› Author AffiliationsFinancial support was granted by the ‘Hundred Talents Program’ of the Harbin Institute of Technology (HIT), the ‘Fundamental Research Funds for the Central University’ (HIT.BRETIV.201502), the NSFC (21202027), the NCET (NCET-12-0145), the Open Project Program of Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology (no. opp2015ZD01), and the ‘Technology Foundation for Selected Overseas Chinese Scholar’ of the Ministry of Human Resources and Social Security of China (MOHRSS).
Further Information

Publication History

Received: 28 April 2017

Accepted after revision: 22 May 2017

Publication Date:
12 June 2017 (online)

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Dedicated to Professor Herbert Mayr on the occasion of his 70th birthday

Abstract

Preliminarily studies on cyclic diacyl peroxides have shown novel and superior reactivities compared with their acyclic diacyl peroxide counterparts in many reaction types. After summarizing the methods available for the preparation of cyclic diacyl peroxides and describing their structural features, this review brings together an overview of their reactivities with respect to oxidations and decarboxylations, and demonstrates the advantages of reactions with cyclic diacyl peroxides, which include metal-free, additive-free, milder conditions, higher yields and better selectivities.

1 Introduction

2 Methods of Preparation of Cyclic Diacyl Peroxides

3 Structures and Stabilities of Cyclic Diacyl Peroxides

4 Oxidation Reactions

4.1 Oxidative Additions to Alkenes

4.2 Oxidation Reactions of Heteroatoms

4.3 Oxidation Reactions of 1,3-Dicarbonyl Compounds

4.4 Hydroxylations of Arenes

5 Decarboxylations

6 Conclusion

Key words

cyclic diacyl peroxides - oxidations - decarboxylations - hydroxylations - cyclizations