Synthesis 2019; 51(14): 2821-2828
DOI: 10.1055/s-0037-1611872
short review
© Georg Thieme Verlag Stuttgart · New York

New Alkene Cyclopropanation Reactions Enabled by Photoredox Catalysis via Radical Carbenoids

Ana G. Herraiz
a  Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Països Catalans 16, 43007 Tarragona, Spain   Email: mgsuero@iciq.es
b  Universitat Rovira i Virgili, Departament de Química Analítica i Química Orgánica, c/Marcelli Domingo 1, 43007 Tarragona, Spain
,
Marcos G. Suero*
a  Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Països Catalans 16, 43007 Tarragona, Spain   Email: mgsuero@iciq.es
› Author Affiliations
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 (eFirst)

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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