可见光促进的苯及衍生物去芳构化反应

doi:10.7503/cjcu20200205

高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (7): 1407.doi: 10.7503/cjcu20200205

• 庆祝《高等学校化学学报》复刊40周年专栏 • 上一篇下一篇

可见光促进的苯及衍生物去芳构化反应

朱敏^1,²,张霄¹,游书力^1,^2,^*()

1.中国科学院上海有机化学研究所金属有机化学国家重点实验室, 上海 200032
2.上海科技大学物质科学与技术学院, 上海 201210

收稿日期:2020-04-14 出版日期:2020-07-10 发布日期:2020-06-10
通讯作者: 游书力 E-mail:slyou@sioc.ac.cn
基金资助:
国家自然科学基金(21821002);国家自然科学基金(21801248);上海市扬帆计划(18YF1428900)

Visible-light-promoted Dearomatization of Benzene and Derivatives^†

ZHU Min^1,²,ZHANG Xiao¹,YOU Shuli^1,^2,^*()

1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China
2. School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China

Received:2020-04-14 Online:2020-07-10 Published:2020-06-10
Contact: Shuli YOU E-mail:slyou@sioc.ac.cn
Supported by:
† National Natural Science Foundation of China(21821002);National Natural Science Foundation of China(21801248);Shanghai Sailing Program for Generous Financial Support, China(18YF1428900)

摘要/Abstract

摘要：

总结了近年来可见光促进苯及其衍生物去芳构化反应的研究进展, 主要分为基态与激发态化学两方面, 并对该领域的发展前景进行了展望.

关键词: 苯, 去芳构化, 能量转移, 单电子转移: 可见光

Abstract:

Benzene rings are widely found in petrochemicals, which are cheap and readily available. Compared with other (hetero)aromatic rings, the dearomatization of benzene rings is more challenging as benzene is more stable. On the other hand, visible-light photocatalysis has experienced rapid development since last decade. Upon visible-light irradiation, highly active intermediates are formed to break aromatic stability and to construct three-dimensional molecules from flat compounds. In this review, recent examples on visible-light-promoted dearomatization of benzene and derivatives are summarized, which can be divided into two main categories: ground-state chemistry and excited-state chemistry. The perspective for future development of this field is also discussed.

Key words: Benzene, Dearomatization, Energy transfer, Single electron transfer, Visible light

中图分类号:

O627

TrendMD:

朱敏, 张霄, 游书力. 可见光促进的苯及衍生物去芳构化反应. 高等学校化学学报, 2020, 41(7): 1407.

ZHU Min, ZHANG Xiao, YOU Shuli. Visible-light-promoted Dearomatization of Benzene and Derivatives^†. Chem. J. Chinese Universities, 2020, 41(7): 1407.

图/表 8

Scheme 1 Selected natural products synthesized with dearomatization reaction as the key step

Scheme 3 General reaction(A), substrate scope(B) and proposed mechanism(C) of visible-light-induced dearomative 1,4-hydroboration of electron-poor benzenes[23] Copyright 2020, American Chemical Society.

Scheme 6 Optimized reaction conditions(A) and proposed mechanism(B) of arenophile-mediated, Ni-catalyzed dearomative trans-1,2-carboamination of benzene derivatives[27] Copyright 2018, American Chemical Society.

Scheme 7 General reaction(A) and substrate scope(B) of visible-light-mediated [4+2] dearomative cycloaddition of pyridine and benzene derivatives via energy transfer[32] Copyright 2019, Elesevier Company.

Scheme 8 General reaction(A), substrate scope(B) and proposed mechanism(C) of visible-light-promoted double functionalization of benzenes via energy transfer[33] Copyright 2019, American Chemical Society.

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可见光促进的苯及衍生物去芳构化反应

Visible-light-promoted Dearomatization of Benzene and Derivatives^†

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可见光促进的苯及衍生物去芳构化反应

Visible-light-promoted Dearomatization of Benzene and Derivatives†

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参考文献 33

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Visible-light-promoted Dearomatization of Benzene and Derivatives^†