Organic Chemistry Portal



Functionalization of 1N-Protected Tetrazoles by Deprotonation with the Turbo Grignard Reagent

Konstantinos Grammatoglou and Aigars Jirgensons*

*Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, Latvia, Email:

K. Grammatoglou, A. Jirgensons, J. Org. Chem., 2022, 87, 3810-3816.

DOI: 10.1021/acs.joc.1c02926

see article for more reactions


1N-PMB-protected tetrazoles undergo C-H deprotonation with the turbo Grignard reagent without retro [2 + 3] cycloaddition as side reaction to provide a metalated intermediate, that can be used for reactions with electrophiles such as aldehydes, ketones, Weinreb amides, and iodine. The PMB-protecting group at the tetrazole can be cleaved using oxidative hydrogenolysis and acidic conditions.

see article for more examples

Deprotection of the 1N-PMB Group in Tetrazole Derivatives

Key Words


ID: J42-Y2022