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Defunctionalisation catalysed by boron Lewis acids

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Abstract

Selective defunctionalisation of organic molecules to valuable intermediates is a fundamentally important transformation in organic synthesis. Despite the advances made in efficient and selective defunctionalisation using transition-metal catalysis, the cost, toxicity, and non-renewable properties limit its application in industrial manufacturing processes. In this regard, boron Lewis acid catalysis has emerged as a powerful tool for the cleavage of carbon–heteroatom bonds. The ground-breaking finding is that the strong boron Lewis acid B(C6F5)3 can activate Si–H bonds through η1 coordination, and this Lewis adduct is a key intermediate that enables various reduction processes. This system can be tuned by variation of the electronic and structural properties of the borane catalyst, and together with different hydride sources high chemoselectivity can be achieved. This Perspective provides a comprehensive summary of various defunctionalisation reactions such as deoxygenation, decarbonylation, desulfurisation, deamination, and dehalogenation, all of which catalysed by boron Lewis acids.

Graphical abstract: Defunctionalisation catalysed by boron Lewis acids

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Article information


Submitted
06 Jul 2020
Accepted
22 Jul 2020
First published
28 Jul 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
Perspective

Defunctionalisation catalysed by boron Lewis acids

H. Fang and M. Oestreich, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC03712E

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