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

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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

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Publication details

The article was received on 20 Mar 2018, accepted on 06 May 2018 and first published on 09 May 2018


Article type: Paper
DOI: 10.1039/C8OB00687C
Citation: Org. Biomol. Chem., 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C8OB00687C

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