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Synthesis 2019; 51(14): 2821-2828
DOI: 10.1055/s-0037-1611872
DOI: 10.1055/s-0037-1611872
short review
New Alkene Cyclopropanation Reactions Enabled by Photoredox Catalysis via Radical Carbenoids
The ICIQ Starting Career Programme, Agencia Estatal de Investigación of the Ministerio de Ciencia e Innovación (CTQ2016-75311-P, AEI/FEDER-EU), the CELLEX Foundation through the CELLEX-ICIQ high-throughput experimentation platform and the CERCA Programme (Generalitat de Catalunya) are gratefully acknowledged for financial support. We thank the CELLEX Foundation for a predoctoral fellowship to A.G.H. M.G.S. is very grateful to the organizing committee of the 2018 Bürgenstock Conference and the Swiss Chemical Society for a JSP fellowship.Further Information
Publication History
Received: 11 March 2019
Accepted after revision: 04 June 2019
Publication Date:
11 June 2019 (online)
Published as part of the Bürgenstock Special Section 2018 Future Stars in Organic Chemistry
Abstract
We describe the recent emergence of a new approach for the synthesis of cyclopropane rings by means of photoredox catalysis. This methodology relies on the photocatalytic generation of radical carbenoids or carbenoid-like radicals as cyclopropanating species, and is characterized by excellent functional group tolerance, chemoselectivity and the ability to form cyclopropanes with excellent control from E/Z alkene mixtures. The mild reaction conditions and employment of user-friendly reagents are highly attractive features that may lead to this approach being used in academic and industrial laboratories.
1 Introduction
2 Photoredox-Catalyzed Alkene Cyclopropanations with Radical Carbenoids
3 Conclusions and Outlook
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For reviews on cyclopropanation reactions, see:
For recent selected examples, see:
For recent reviews, see:
The use of diiodomethane under UV-light irradiation for cyclopropanation reactions was firstly carried out by Simmons and Kropp; an iodomethyl radical (•)CH2I and an iodomethyl cation (+)CH2I were proposed as reactive intermediates:
Later, density functional theory investigations performed by Phillips and co-workers suggested iso-diiodomethane (CH2=I–I) as an intermediate:
For alternative reports of alkene cyclopropanations enabled by photoredox catalysis that do not involve radical carbenoids, see:
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