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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.

SUBMITTER: Hidalgo N

PROVIDER: S-EPMC10988615 | biostudies-literature | 2024 Apr

REPOSITORIES: biostudies-literature

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

Hidalgo Nereida N Le Gac Arnaud A Mallet-Ladeira Sonia S Bouhadir Ghenwa G Bourissou Didier D

Chemical science 20240301 14

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 ...[more]

PMID: 38577365

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