Issue 14, 2024

Chemo-selective Stille-type coupling of acyl-chlorides upon phosphine-borane Au(i) catalysis

Abstract

Phosphine-boranes do not promote oxidative addition of acyl chlorides to gold, but the phosphine-borane gold triflimide complex [iPr2P(o-C6H4)BCy2]AuNTf2 was found to catalyze the coupling of acyl chlorides and aryl stannanes. The reaction involves aryl/chloride-bridged dinuclear gold(I) complexes as key intermediates, as substantiated by spectroscopic and crystallographic analyses. Similar to Pd(0)/Pd(II)-catalyzed Stille coupling with phosphine-borane ligands, the gold-catalyzed variant shows complete chemoselectivity for acyl chlorides over aryl iodides and bromides, enabling straightforward access to halogenated aryl ketones.

Graphical abstract: Chemo-selective Stille-type coupling of acyl-chlorides upon phosphine-borane Au(i) catalysis

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Article information

Article type
Edge Article
Submitted
17 Nov 2023
Accepted
26 Feb 2024
First published
01 Mar 2024
This article is Open Access

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

Chem. Sci., 2024,15, 5187-5191

Chemo-selective Stille-type coupling of acyl-chlorides upon phosphine-borane Au(I) catalysis

N. Hidalgo, A. Le Gac, S. Mallet-Ladeira, G. Bouhadir and D. Bourissou, Chem. Sci., 2024, 15, 5187 DOI: 10.1039/D3SC06193K

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