Kinetics and Mechanism of the Platinum(II)‐Catalyzed Hydroarylation of Vinyl Arenes with 1,2‐Dimethylindole

Abstract

The mechanism of the intermolecular hydroarylation of vinyl arenes (1) with 1,2-dimethylindole (2) catalyzed by PtCl 2 has been evaluated through a combination of kinetic analysis, deuterium labeling studies, and stereochemical analysis. The results of these and additional experiments are consistent with a mechanism for hydroarylation involving rapid and reversible complexation of vinyl arene to the catalytically inactive platinum mono(vinyl arene)complex trans-PtCl 2 (H 2 C=CHAr)(solvent) to form the reactive platinum bis(vinyl arene) complex trans-PtCl 2 (H 2 C=CHAr) 2 , which undergoes turnover-limiting, outer-sphere attack of indole. Rapid protodemetallation of the resulting platinum alkyl complex releases product and regenerates the equilibrating mixture of platinum π-vinyl arene complexes. Scheme 4. Platinum-catalyzed reaction of 2 with trans-1 b-d 2 .Scheme 5. Platinum-catalyzed intramolecular hydroarylation of 6-d 2 .

Research progress in stable interfacial constructions between composite polymer electrolytes and electrodes

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