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A Study of the Reactivity of (Aza‐)Quinone Methides in Selective C6‐Alkylations of Indoles
Author(s) -
Yan Jiyao,
Zhang Zhihan,
Chen Min,
Lin Zhenyang,
Sun Jianwei
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202000850
Subject(s) - electrophile , alkylation , reactivity (psychology) , chemistry , quinone , indole test , selectivity , combinatorial chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
The kinetic and thermodynamic features of indole N1‐ and C6‐alkylation reactions with (aza‐)quinone methides have been studied. The electrophilic reactivity of these quinone methides have also been compared for the first time by both experiments and DFT calculations. The indole N1‐alkylation is typically kinetically favorable, but the C6‐alkylation is more thermodynamically favorable. With suitable conditions, the C6‐alkylation could be achieved with high efficiency and selectivity. Among these quinone methides, the reactivity increases from aza‐p‐QMs to o‐QMs. The results not only provide access to a range of valuable triarylmethanes, but also guide future development of new reactions with these versatile electrophiles.