Issue 8, 2020

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
25 11 2019
Accepted
09 1 2020
First published
13 1 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2020,11, 2136-2140

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, 11, 2136 DOI: 10.1039/C9SC05970A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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