Synthesis 2019; 51(02): 303-333
DOI: 10.1055/s-0037-1610329
review
© Georg Thieme Verlag Stuttgart · New York

Acyl Radical Chemistry via Visible-Light Photoredox Catalysis

Arghya Banerjee
a  Department of Chemistry, Stony Brook University, Stony Brook, New York, 11794-3400, USA
,
Zhen Lei
a  Department of Chemistry, Stony Brook University, Stony Brook, New York, 11794-3400, USA
,
Ming-Yu Ngai*
a  Department of Chemistry, Stony Brook University, Stony Brook, New York, 11794-3400, USA
b  Institute of Chemical Biology and Drug Discovery, Stony Brook University, Stony Brook, New York, 11794-3400, USA
› Author Affiliations
We thank the National Institute of General Medical Sciences (R35GM119652) for supporting our research.
Further Information

Publication History

Received: 31 August 2018

Accepted after revision: 19 October 2018

Publication Date:
12 December 2018 (online)


These authors contributed equally to this work.

Abstract

Visible-light photoredox catalysis enables easy access to acyl radicals under mild reaction conditions. Reactive acyl radicals, generated from various acyl precursors such as aldehydes, α-keto acids, carboxylic acids, anhydrides, acyl thioesters, acyl chlorides, or acyl silanes, can undergo a diverse range of synthetically useful transformations, which were previously difficult or inaccessible. This review summarizes the recent progress on visible-light-driven acyl radical generation using transition-metal photoredox catalysts, metallaphotocatalysts, hypervalent iodine catalysts or organic photocatalysts.

1 Introduction

2 The Scope of This Review

3 Aldehydes as a Source of Acyl Radicals

4 α-Keto Acids as a Source of Acyl Radicals

5 Carboxylic Acids as a Source of Acyl Radicals

6 Anhydrides as a Source of Acyl Radicals

7 Acyl Thioesters as a Source of Acyl Radicals

8 Acyl Chlorides as a Source of Acyl Radicals

9 Acyl Silanes as a Source of Acyl Radicals

10 Conclusions and Future Outlook

 
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