Rhodium-catalysed decarbonylative C(sp2)-H alkylation of indolines with alkyl carboxylic acids and carboxylic anhydrides under redox-neutral conditions

Org Biomol Chem. 2022 Apr 6;20(14):2808-2812. doi: 10.1039/d2ob00249c.

Abstract

We developed a rhodium-catalysed decarbonylative C(sp2)-H alkylation method for indolines. This reaction facilitates the use of alkyl carboxylic acids and their anhydrides as a cheap, abundant and non-toxic alkyl source under redox-neutral conditions, featuring the introduction of a primary alkyl chain, which cannot be addressed by previous radical-mediated decarboxylative reaction. Through a mechanistic investigation, we revealed that an initially formed C-7 acylated indoline was transformed into the corresponding alkylated indoline via a decarbonylation process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Anhydrides
  • Carboxylic Acids
  • Indoles
  • Oxidation-Reduction
  • Rhodium*

Substances

  • Anhydrides
  • Carboxylic Acids
  • Indoles
  • indoline
  • Rhodium