Ligand-Assisted Gold-Catalyzed Cross-Coupling with Aryldiazonium Salts: Redox Gold Catalysis without an External Oxidant

被引:127
作者
Cai, Rong [1 ]
Lu, Mei [2 ]
Aguilera, Ellen Y. [1 ]
Xi, Yumeng [1 ]
Akhmedov, Novruz G. [1 ]
Petersen, Jeffrey L. [1 ]
Chen, Hao [2 ]
Shi, Xiaodong [1 ]
机构
[1] Univ Virginia, C Eugene Bennett Dept Chem, Morgantown, WV 26506 USA
[2] Ohio Univ, Dept Chem & Biochem, Athens, OH 45701 USA
基金
美国国家科学基金会;
关键词
aryldiazonium salt; cross-coupling; gold; redox catalysis; IONIZATION MASS-SPECTROMETRY; OXIDATIVE ADDITION; TERMINAL ALKYNES; DIAZONIUM SALTS; BORONIC ACIDS; REACTIVITY; COMPLEXES; ALKENES; ACTIVATION; PHOTOREDOX;
D O I
10.1002/anie.201503546
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Gold-catalyzed C(sp)-C(sp(2)) and C(sp(2))-C(sp(2)) cross-coupling reactions are accomplished with aryldiazonium salts as the coupling partner. With the assistance of bpy ligand, gold(I) species were oxidized to gold(III) by diazonium without any external oxidants. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the nitrogen extrusion followed by Au-III reductive elimination as the key step.
引用
收藏
页码:8772 / 8776
页数:5
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