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Synthesis of 1,3-disubstituted bicyclo[1.1.0]butanes via directed bridgehead functionalization

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Abstract

Bicyclo[1.1.0]butanes (BCBs) are increasingly valued as intermediates in ‘strain release’ chemistry for the synthesis of substituted four membered rings and bicyclo[1.1.1]pentanes, with applications including bioconjugation processes. Variation of the BCB bridgehead substituents can be challenging due to the inherent strain of the bicyclic scaffold, often necessitating linear syntheses of specific BCB targets. Here we report the first palladium catalyzed cross-coupling on pre-formed BCBs which enables a ‘late stage’ diversification of the bridgehead position, and the conversion of the resultant products into a range of useful small ring building blocks.

Graphical abstract: Synthesis of 1,3-disubstituted bicyclo[1.1.0]butanes via directed bridgehead functionalization

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Article information


Submitted
01 Apr 2021
Accepted
26 Apr 2021
First published
27 Apr 2021

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021, Advance Article
Article type
Edge Article

Synthesis of 1,3-disubstituted bicyclo[1.1.0]butanes via directed bridgehead functionalization

R. E. McNamee, M. M. Haugland, J. Nugent, R. Chan, K. E. Christensen and E. A. Anderson, Chem. Sci., 2021, Advance Article , DOI: 10.1039/D1SC01836A

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