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Aldehydes and ketones influence reactivity and selectivity in nickel-catalysed Suzuki–Miyaura reactions§

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Abstract

The energetically-favorable coordination of aldehydes and ketones – but not esters or amides – to Ni0 during Suzuki–Miyaura reactions can lead either to exquisite selectivity and enhanced reactivity, or to inhibition of the reaction. Aryl halides where the C–X bond is connected to the same π-system as an aldehyde or ketone undergo unexpectedly rapid oxidative addition to [Ni(COD)(dppf)] (1), and are selectively cross-coupled during competition reactions. When aldehydes and ketones are present in the form of exogenous additives, the cross-coupling reaction is inhibited to an extent that depends on the strength of the coordination of the pendant carbonyl group to Ni0. This work advances our understanding of how common functional groups interact with Ni0 catalysts and how these interactions affect workhorse catalytic reactions in academia and industry.

Graphical abstract: Aldehydes and ketones influence reactivity and selectivity in nickel-catalysed Suzuki–Miyaura reactions

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Article information


Submitted
28 Oct 2019
Accepted
04 Jan 2020
First published
06 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

Aldehydes and ketones influence reactivity and selectivity in nickel-catalysed Suzuki–Miyaura reactions

A. K. Cooper, D. K. Leonard, S. Bajo, P. M. Burton and D. J. Nelson, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC05444H

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