Citation: Yan-Li Li, Zhi-Ming Li, Kai-Kai Wang, Xiao-Long He. Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides[J]. Chinese Chemical Letters, ;2024, 35(7): 109322. doi: 10.1016/j.cclet.2023.109322 shu

Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides

Yan-Li Li ^a ,
Zhi-Ming Li ^c ,
Kai-Kai Wang ^{b, *,} ,
Xiao-Long He ^{c, *,}

a.
Medical College, Xinxiang University, Xinxiang 453000, China
b.
School of Pharmacy, Xinxiang University, Xinxiang 453000, China
c.
School of Food and Bioengineering, Xihua University, Chengdu 610039, China

wangkaikaii@163.com

xlhe1021@sina.com

Received Date: 28 August 2023
Revised Date: 7 November 2023
Accepted Date: 16 November 2023
Available Online: 19 November 2023

Figures(53)

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 conjugate 1,6- 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.
- Conjugate addition,
- QMs,
- IIMs,
- LUMO,
- Remote activation,
- Dearomative addition
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沈阳化工大学材料科学与工程学院沈阳 110142