Journal
NEW JOURNAL OF CHEMISTRY
Volume 47, Issue 12, Pages 5930-5938Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3nj00451a
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This paper reports group 11 metal complexes of a guanidine-substituted triphenylphosphine, which were used as precatalysts in various reactions. The complexes showed promising catalytic activity and stability, making them attractive for further research and applications.
Phosphines bearing guanidine substituents at the backbone are attractive hybrid ligands that have not yet received adequate attention. This paper describes group 11 metal complexes of a guanidine-substituted triphenylphosphine, viz., N '' -[2-(diphenylphosphino)phenyl]-N,N ' -diisopropylguanidine (1). Reactions of 1 with Cu(I) and Ag(I) precursors yielded the P,N-chelate complexes [M(1-k(2)P,N)(2)]X, where M/X = Cu/BF4, Cu/Br, Ag/SbF6 and Ag/Br. Conversely, reacting 1 and the hydrochloride 1 center dot HCl with [AuCl(SMe2)] produced the corresponding phosphine complexes [AuCl(1-kappa P)] and [AuCl(1H-kappa P)]Cl, which were further converted into [{mu(P,N)-1}(2)Au-2][SbF6](2) and [AuCl(1H-kappa P)][SbF6], respectively, by reacting with Ag[SbF6]. These compounds and the bis-phosphine complex [Au(1-kappa P)(2)][SbF6] were studied as precatalysts in the Au-mediated cyclisation of N-propargylbenzamide and the addition of benzoic acid across terminal alkynes. Of the Au(I)-1 complexes studied, the complex [{mu(P,N)-1}(2)Au-2][SbF6](2) was particularly attractive as a stable and well-defined, silver-free precatalyst, which can be conveniently activated in situ by the addition of a protic acid (either as an additive or a substrate).
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