The conjugate addition of in-situ generated(aza-)quinone methides(QMs)and indole imine methides(IIMs)emerged as a powerful protocol to access densely functionalized benzenes and indoles.Hydroxybenzyl alcohols,aminoben...The conjugate addition of in-situ generated(aza-)quinone methides(QMs)and indole imine methides(IIMs)emerged as a powerful protocol to access densely functionalized benzenes and indoles.Hydroxybenzyl alcohols,aminobenzhydryl alcohols,and varied indolylmethanols served as most effective precursors for the in-situ generation of such reactive species under acid conditions.The relevant propargylic alcohol has proven to be an elegant precursor to generate the propargylic-QMs and-IIMs via the acid promoted dehydration process,thus enabling diverse challenging remote activation to proceed conjugate1,6-and 1,8-additions.Moreover,the heteroarene has proven to be workable to transfer the LUMO of the p-QMs and 2-IIMs,thus inducing the remote nucleophilic dearomative additions.The conjugate additions of(aza-)p-QMs and varied IIMs has made significant contribution in the field of remote activation chemistry in past decade.This review summarizes the latest advances of the remote conjugate additions of the in-situ generated QMs and IIMs.展开更多
基金the financial support from the National Natural Science Foundation of China(No.22001216)the Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province(No.CSPC202315)+2 种基金the Science and Technology Department of Sichuan Province,China(No.2022NSFSC1203)the Higher Education Institution Key Research Project Plan of Henan Province(No.24B150031)the Program for Youth Backbone Teacher Training in University of Henan Province(No.2021GGJS163)。
文摘The conjugate addition of in-situ generated(aza-)quinone methides(QMs)and indole imine methides(IIMs)emerged as a powerful protocol to access densely functionalized benzenes and indoles.Hydroxybenzyl alcohols,aminobenzhydryl alcohols,and varied indolylmethanols served as most effective precursors for the in-situ generation of such reactive species under acid conditions.The relevant propargylic alcohol has proven to be an elegant precursor to generate the propargylic-QMs and-IIMs via the acid promoted dehydration process,thus enabling diverse challenging remote activation to proceed conjugate1,6-and 1,8-additions.Moreover,the heteroarene has proven to be workable to transfer the LUMO of the p-QMs and 2-IIMs,thus inducing the remote nucleophilic dearomative additions.The conjugate additions of(aza-)p-QMs and varied IIMs has made significant contribution in the field of remote activation chemistry in past decade.This review summarizes the latest advances of the remote conjugate additions of the in-situ generated QMs and IIMs.
