CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1063-1072
DOI: 10.1055/s-0037-1611658
short review
Copyright with the author

Advancements in Visible-Light-Enabled Radical C(sp)2–H Alkylation of (Hetero)arenes

Alexandra C. Sun
,
Rory C. McAtee
,
Edward J. McClain
,
Willard Henry Dow Laboratory, Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109, USA   Email: crjsteph@umich.edu
› Author Affiliations
The authors acknowledge the financial support for this work from the NIH NIGMS (R01-GM127774) and the University of Michigan. This work is supported by an NSF Graduate Research Fellowship for A.C.S. and R.C.M. (grant DGE 1256260).
Further Information

Publication History

Received: 18 December 2018

Accepted: 20 December 2018

Publication Date:
25 January 2019 (eFirst)

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

The Minisci reaction, which encompasses the radical C–H alkylation of heteroarenes, has undergone revolutionary development in recent years. The application of photoredox catalysis to alkyl radical generation has given rise to a multitude of methods that feature enhanced functional group tolerance, generality, and operational simplicity. The intent of this short review is to bring readers up to date on this rapidly expanding field. Specifically, we will highlight key examples of visible-light-driven Minisci alkylation strategies that represent key advancements in this area of research. The scope and limitations of these transformations will be discussed, with a focus on examining the underlying pathways for alkyl radical generation. Our goal is to make this short review a stepping stone for further synthetic research development. Sections are organized based on alkyl radical precursor reagents.

1 Introduction

2 Alkyl Carboxylic Acids and Carboxylic Acid Derivatives

3 Alkylboronic Acids

4 Potassium Alkyl- and Alkoxymethyltrifluoroborates

5 Alkyl Halides

6 Alcohols and Ethers

7 Conclusion

 
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