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

Publication ,  Journal Article
Zhang, Z; Liu, S; Widenhoefer, RA
Published in: Israel Journal of Chemistry
March 1, 2020

The mechanism of the intermolecular hydroarylation of vinyl arenes (1) with 1,2-dimethylindole (2) catalyzed by PtCl2 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-PtCl2(H2C=CHAr)(solvent) to form the reactive platinum bis(vinyl arene) complex trans-PtCl2(H2C=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.

Duke Scholars

Published In

Israel Journal of Chemistry

DOI

EISSN

1869-5868

ISSN

0021-2148

Publication Date

March 1, 2020

Volume

60

Issue

3-4

Start / End Page

437 / 445

Related Subject Headings

  • Chemical Physics
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

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Zhang, Z., Liu, S., & Widenhoefer, R. A. (2020). Kinetics and Mechanism of the Platinum(II)-Catalyzed Hydroarylation of Vinyl Arenes with 1,2-Dimethylindole. Israel Journal of Chemistry, 60(3–4), 437–445. https://doi.org/10.1002/ijch.201900065
Zhang, Z., S. Liu, and R. A. Widenhoefer. “Kinetics and Mechanism of the Platinum(II)-Catalyzed Hydroarylation of Vinyl Arenes with 1,2-Dimethylindole.” Israel Journal of Chemistry 60, no. 3–4 (March 1, 2020): 437–45. https://doi.org/10.1002/ijch.201900065.
Zhang Z, Liu S, Widenhoefer RA. Kinetics and Mechanism of the Platinum(II)-Catalyzed Hydroarylation of Vinyl Arenes with 1,2-Dimethylindole. Israel Journal of Chemistry. 2020 Mar 1;60(3–4):437–45.
Zhang, Z., et al. “Kinetics and Mechanism of the Platinum(II)-Catalyzed Hydroarylation of Vinyl Arenes with 1,2-Dimethylindole.” Israel Journal of Chemistry, vol. 60, no. 3–4, Mar. 2020, pp. 437–45. Scopus, doi:10.1002/ijch.201900065.
Zhang Z, Liu S, Widenhoefer RA. Kinetics and Mechanism of the Platinum(II)-Catalyzed Hydroarylation of Vinyl Arenes with 1,2-Dimethylindole. Israel Journal of Chemistry. 2020 Mar 1;60(3–4):437–445.
Journal cover image

Published In

Israel Journal of Chemistry

DOI

EISSN

1869-5868

ISSN

0021-2148

Publication Date

March 1, 2020

Volume

60

Issue

3-4

Start / End Page

437 / 445

Related Subject Headings

  • Chemical Physics
  • 34 Chemical sciences
  • 03 Chemical Sciences