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

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.