Cp*Rh(III)-Catalyzed C-H Bond Difluorovinylation of Indoles with α,α-Difluorovinyl Tosylate

J Org Chem. 2019 Jun 7;84(11):7320-7330. doi: 10.1021/acs.joc.9b00957. Epub 2019 May 29.

Abstract

Unprecedented Rh(III)-catalyzed C-H bond difluorovinylation of indoles has been successfully developed, and this method provided an example of direct difluorovinylation reaction through C-H bond activation which was rarely reported. In this context, N-ethoxycarbamoyl served as the directing group and 2,2-difluorovinyl tosylates were used for the construction of difluorovinyl-substituted indoles. This method provided a practical strategy for difluorovinylation of indoles with moderate to good yields and is characterized by the broad synthetic utility, mild conditions, and high efficiency.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzenesulfonates / chemistry*
  • Catalysis
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Indoles / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Rhodium / chemistry*

Substances

  • 4-methylbenzenesulfonic acid
  • Benzenesulfonates
  • Hydrocarbons, Fluorinated
  • Indoles
  • Organometallic Compounds
  • Rhodium