期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 27, 期 46, 页码 11989-11996出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202101751
关键词
chloride abstraction; hydrogen bond; gold; kinetics; phosphine ligands
资金
- European Union (Horizon 2020 Marie Skodowska-Curie COFUND postdoctoral fellowship) [754510]
- European Research Council [835080]
- Ministerio de Ciencia e Innovacion [PID2019-104815GB-I00, CEX2019-000925-S]
- AGAUR [2017 SGR 1257]
- CERCA Program/Generalitat de Catalunya
A library of gold(I) chloride complexes with phosphine ligands incorporating (thio)urea and squaramide H-bond donors was prepared to promote chloride abstraction from Au(I) via H-bonding. In the absence of silver additives, complexes bearing squaramides and trifluoromethylated aromatic ureas displayed good catalytic activity in various reactions, including cyclization and tandem reactions. Kinetic studies and DFT calculations suggest that the reaction's energy span is influenced by both the chloride abstraction step and subsequent cyclization step facilitated by the bidentate H-bond donor.
A library of gold(I) chloride complexes with phosphine ligands incorporating pendant (thio)urea and squaramide H-bond donors was prepared with the aim of promoting chloride abstraction from Au(I) via H-bonding. In the absence of silver additives, complexes bearing squaramides and trifluoromethylated aromatic ureas displayed good catalytic activity in the cyclization of N-propargyl benzamides, as well as in a 1,6-enyne cycloisomerization, a tandem cyclization-indole addition reaction and the hydrohydrazination of phenylacetylene. Kinetic studies and DFT calculations indicate that the energetic span of the reaction is accounted by both the chloride abstraction step, facilitated by the bidentate H-bond donor via an associative mechanism, and the subsequent cyclization step.
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