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Published in

American Association for the Advancement of Science, Science Advances, 37(9), 2023

DOI: 10.1126/sciadv.adj2486

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Wittig/B─H insertion reaction: A unique access to trisubstituted Z -alkenes

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

The Wittig reaction, which is one of the most effective methods for synthesizing alkenes from carbonyl compounds, generally gives thermodynamically stable E -alkenes, and synthesis of trisubstituted Z -alkenes from ketones presents notable challenges. Here, we report what we refer to as Wittig/B─H insertion reactions, which innovatively combine a Wittig reaction with carbene insertion into a B─H bond and constitute a promising method for the synthesis of thermodynamically unstable trisubstituted Z -boryl alkenes. Combined with the easy transformations of boryl group, this methodology provides efficient access to a variety of previously unavailable trisubstituted Z -alkenes and thus provides a platform for discovery of pharmaceuticals. The unique Z- selectivity of the reaction is determined by the maximum overlap of the orbitals between the B─H bond of the borane adduct and the alkylidene carbene intermediate in the transition state.