New Alkene Cyclopropanation Reactions Enabled by Photoredox Catalysis via Radical Carbenoids

Ana G. Herraiz; Marcos G. Suero

doi:10.1055/s-0037-1611872

Synthesis, Table of Contents

Synthesis 2019; 51(14): 2821-2828
DOI: 10.1055/s-0037-1611872

short review

New Alkene Cyclopropanation Reactions Enabled by Photoredox Catalysis via Radical Carbenoids

Ana G. Herraiz

^aInstitute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Països Catalans 16, 43007 Tarragona, Spain Email: mgsuero@iciq.es

^bUniversitat Rovira i Virgili, Departament de Química Analítica i Química Orgánica, c/Marcelli Domingo 1, 43007 Tarragona, Spain

,

Marcos G. Suero*

^aInstitute 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

Abstract

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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

Key words

photoredox catalysis - radicals - carbenoids - cyclopropanes - cyclopropanation

Full Text

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