Organic Chemistry Portal



Radical-Mediated Strategies for the Functionalization of Alkenes with Diazo Compounds

Yong-Liang Su, Geng-Xin Liu, Jun-Wen Liu, Linh Tram, Huang Qiu* and Michael P. Doyle*

*Sun Yat-sen University, Guangzhou 510006, China; The University of Texas at San Antonio, San Antonio, Texas 78249, United States, Email:,

Y.-L. Su, G.-X. Liu, J.-W. Liu, L. Tram, H. Qiu, M. P. Doyle, J. Am. Chem. Soc., 2020, 142, 13846-13855.

DOI: 10.1021/jacs.0c05183

see article for more reactions


A radical-mediated addition strategy of diazo compounds to diverse alkenes achieves a difunctionalization - either through hydroalkylation by thiol-assisted hydrogen atom transfer (HAT) or formation of azidoalkylation products through an iron catalytic cycle. The methods proceed under mild reaction conditions and show high functional group tolerance.

see article for more examples

Key Words

substituted esters, photochemistry, Hantzsch ester

ID: J48-Y2020