Assessing the Role of Counterion in Gold-Catalyzed Dearomatization of Indoles with Allenamides by NMR Studies

被引:72
作者
Rocchigiani, Luca [1 ,2 ]
Jia, Minqiang [3 ]
Bandini, Marco [3 ]
Macchioni, Alceo [1 ,2 ,4 ]
机构
[1] Univ Perugia, Dept Chem Biol & Biotechnol, I-06123 Perugia, Italy
[2] CIRCC, I-06123 Perugia, Italy
[3] Alma Mater Studiorum Univ Bologna, Dept Chem G Ciamician, I-40126 Bologna, Italy
[4] Univ Perugia, Dept Chem Biol & Biotechnol, Ist Sci & Tecnol Mol CNR CNR ISTM, I-06123 Perugia, Italy
关键词
gold; NMR spectroscopy; anion effect; mechanism; weak interactions; homogeneous catalysis; TRANSITION-METAL CATALYSIS; CROSS-COUPLING REACTIONS; ORGANOMETALLIC CHEMISTRY; ACTIVATION PROCESSES; REACTION-MECHANISM; ORGANIC-REACTIONS; SPECTROSCOPY; COMPLEXES; PLATINUM; ALKYNES;
D O I
10.1021/acscatal.5b00502
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The counterion effect in the gold(I)-catalyzed dearomative condensation of indoles with allenamides is unveiled by means of 1D- and 2D-NMR investigation. The different coordination ability and hydrogen bonding tendency of TFA(-) and OTf- led to specific interactions with the reaction partners dictating the regiodivergent outcome.
引用
收藏
页码:3911 / 3915
页数:5
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