Approach to the Synthesis of Indoline Derivatives from Diaryliodonium Salts

摘要

An effective method of constructing the indoline moiety via intramolecular nucleophilic ring closure of a diaryliodonium salt is described. Diacetoxyiodoarene compounds (1a–1e) were converted into intermediate Koser’s reagent and coupled with arylstannanes (7–10) to form diaryliodonium salts (11a–14e). Indoline compounds with different N-protecting groups, 15, 16, 17, and 18, were synthesized in higher yields by treating salts (11a–14e) with Cs2CO3 and TEMPO. Regardless of the electronic environment of five para-substituted iodoarenes and the natures of four N-protected arylstannane groups, the conversion proceeded well to afford corresponding indolines in yields of 72–84 and 70–84%, respectively.