Jump to main content
Jump to site search

Issue 17, 2019
Previous Article Next Article

Platinum(II)-catalyzed dehydrative C3-benzylation of electron-deficient indoles with benzyl alcohols

Author affiliations

Abstract

A synthetic strategy for the water-promoted direct dehydrative coupling of indoles with benzyl alcohols catalyzed by PtCl2(PhCN)2 in 1,2-dichloroethane has been developed. Water molecules significantly accelerate C–C bond formation, whereas the reaction proceeds slowly under anhydrous conditions. Comparative rate plots for reactions in the presence of H2O and D2O show a kinetic solvent isotope effect (KSIE) of 1.5. A Hammett study of the dehydrative reaction of para-substituted benzhydrols shows negative ρ values, indicating a build-up of cationic charge during the rate-determining sp3 C–O bond cleavage step. Our catalytic system can be used on the gram scale with simplified product isolation and catalysis is performed using 1 mol% of a Pt(II) catalyst with an additional molecule of water.

Graphical abstract: Platinum(ii)-catalyzed dehydrative C3-benzylation of electron-deficient indoles with benzyl alcohols

Back to tab navigation

Supplementary files

Publication details

The article was received on 01 Jul 2019, accepted on 12 Jul 2019 and first published on 17 Jul 2019


Article type: Research Article
DOI: 10.1039/C9QO00831D
Org. Chem. Front., 2019,6, 3150-3157

  •   Request permissions

    Platinum(II)-catalyzed dehydrative C3-benzylation of electron-deficient indoles with benzyl alcohols

    H. Hikawa, Y. Matsuura, S. Kikkawa and I. Azumaya, Org. Chem. Front., 2019, 6, 3150
    DOI: 10.1039/C9QO00831D

Search articles by author

Spotlight

Advertisements