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A borane-mediated palladium-catalyzed reductive allylic alkylation of α,β-unsaturated carbonyl compounds

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Abstract

The development of the palladium-catalyzed allylic alkylation of in situ generated boron enolates via tandem 1,4-hydroboration is reported. Investigation of the reaction revealed insights into specific catalyst electronic features as well as a profound leaving group effect that proved crucial for achieving efficient allylic alkylation of ester enolates at room temperature and ultimately a highly preparatively useful synthesis of notoriously challenging acyclic all-carbon quaternary stereocenters. The method demonstrates boron enolates as viable pro-nucleophiles in transition-metal catalyzed allylic alkylation, potentially opening up further transformations outside their traditional use.

Graphical abstract: A borane-mediated palladium-catalyzed reductive allylic alkylation of α,β-unsaturated carbonyl compounds

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Article information


Submitted
25 Nov 2019
Accepted
09 Jan 2020
First published
13 Jan 2020

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

Chem. Sci., 2020, Advance Article
Article type
Edge Article

A borane-mediated palladium-catalyzed reductive allylic alkylation of α,β-unsaturated carbonyl compounds

B. M. Trost, Z. Zuo, J. E. Schultz, N. Anugula and K. A. Carr, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC05970A

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