Synthesis of Indoline- and 1,2,3,4-Tetrahydroquinoline-Based Symmetrical Triarylmethanes.

ABSTRACT: We present a novel and efficient, metal-free methodology for the regioselective synthesis of symmetrical triarylmethanes through C-H alkylation of indolines and 1,2,3,4-tetrahydroquinolines with aryl aldehydes. The transformation employs 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as both solvent and promoter, eliminating the need for traditional metal catalysts or directing groups. This method demonstrates exceptional regioselectivity, targeting the C5 position of indolines and the C6 position of tetrahydroquinolines exclusively. The protocol exhibits a broad substrate scope, accommodating diverse aryl aldehydes and heterocyclic substrates under mild conditions. Notably, the reaction proceeds efficiently with both N-H-free and N-benzyl-protected substrates. Mechanistic studies, based

SUBMITTER: Taskesenligil Y 

PROVIDER: S-EPMC12281573 | biostudies-literature | 2025 Jul

REPOSITORIES: biostudies-literature