Organic Chemistry Portal



Copper-Catalyzed Carbenoid Insertion Reactions of α-Diazoesters and α-Diazoketones into Si-H and S-H Bonds

Hoda Keipour, Angela Jalba, Léo Delage-Laurin and Thierry Ollevier*

*Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC G1V 0A6, Canada, Email:

H. Keipour, A. Jalba, L. Delage-Laurin, T. Ollevier, J. Org. Chem., 2017, 82, 3000-3010.

DOI: 10.1021/acs.joc.6b02998

see article for more reactions


An efficient copper-catalyzed carbenoid insertion reaction of α-diazo carbonyl compounds into Si-H and S-H bonds provides a broad range of α-silylesters and α-thioesters in high yields using 5 mol% of a simple copper(I) salt as catalyst. In addition, α-diazoketones can be converted to α-silylketones in moderate yields.

see article for more examples

Iron-Catalyzed Carbene Insertion Reactions of α-Diazoesters into Si-H Bonds

H. Keipour, T. Ollevier, Org. Lett., 2017, 19, 5736-5739.

Key Words

Silanes, Aryl Sulfides, Sulfides

ID: J42-Y2017