Issue 47, 2020

Defunctionalisation catalysed by boron Lewis acids

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

Article information

Article type
Perspective
Submitted
06 júl. 2020
Accepted
22 júl. 2020
First published
28 júl. 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, 12604-12615

Defunctionalisation catalysed by boron Lewis acids

H. Fang and M. Oestreich, Chem. Sci., 2020, 11, 12604 DOI: 10.1039/D0SC03712E

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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