Jump to main content
Jump to site search

Issue 21, 2018
Previous Article Next Article

Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1′-diarylbutyl pharmacophore

Author affiliations

Abstract

1,1′-Diarylbutyl groups are a common pharmacophore found in many biologically active small molecules. To access these systems under mild conditions, the reaction of diarylmethyl trichloroacetimidates with allyltributylstannanes was explored. Simply heating allyltributylstannane with the trichloroacetimidate resulted in substitution of the imidate with an allyl group. Unlike other methods used to access these systems, no strong base, transition metal catalyst, Brønsted acid or Lewis acid promoter was required to affect the transformation. Conversions are best with electron rich benzylic trichloroacetimidate systems, where excellent yields are achieved just by refluxing the reactants together in nitromethane.

Graphical abstract: Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1′-diarylbutyl pharmacophore

Back to tab navigation

Supplementary files

Article information


Submitted
20 Mar 2018
Accepted
06 May 2018
First published
09 May 2018

Org. Biomol. Chem., 2018,16, 4008-4012
Article type
Paper
Author version available

Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1′-diarylbutyl pharmacophore

N. S. Mahajani and J. D. Chisholm, Org. Biomol. Chem., 2018, 16, 4008
DOI: 10.1039/C8OB00687C

Social activity

Search articles by author

Spotlight

Advertisements