Restoration of Catalytic Activity by the Preservation of Ligand Structure: Cu-catalysed Asymmetric Conjugate Addition with 1,1-diborylmethane

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 Jun 24

PMID 34163641

Citations 4

Authors

Changhee Kim

Byeongdo Roh

Hong Geun Lee

Affiliations

Soon will be listed here.

Abstract

Reported herein is a novel reaction engineering protocol to enhance the efficiency of a transition metal-catalysed process by strategically preventing ligand degradation. Based on spectroscopic investigations, a decomposition pathway of a chiral phosphoramidite ligand during a Cu-catalysed reaction was identified. The involvement of the destructive process could be minimized under the modified reaction conditions that control the amount of nucleophilic alkoxide base, which is the origin of ligand decomposition. Overall, the strategy has been successfully applied to a new class of asymmetric conjugate addition reactions with bis[(pinacolato)boryl]methane, in which α,β-unsaturated enones are utilised as substrates.

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