Developments in Visible Light Catalyzed Asymmetric Minisci Reactions

doi:10.6023/cjoc202312016

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (7): 2110-2123.DOI: 10.6023/cjoc202312016 Previous Articles Next Articles

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可见光催化不对称Minisci反应研究进展

李文雅^a, 王煜^a, 陈江琦^a, 史丹^b, 张良^a, 余小春^a^,^*(), 王正军^a^,^c^,^*()

a 温州大学化学与材料工程学院浙江温州 325035
b 温州市市场监督管理局温州市质量技术检测科学研究院浙江温州 325052
c 湖南大学化学生物传感与计量学国家重点实验室长沙 430100

收稿日期:2023-12-16 修回日期:2024-02-12 发布日期:2024-03-28
基金资助:
湖南大学化学生物传感与计量学国家重点实验室开放项目(20230767); 温州市基础性科研(G20220020)

Developments in Visible Light Catalyzed Asymmetric Minisci Reactions

Wenya Li^a, Yu Wang^a, Jiangqi Chen^a, Dan Shi^b, Liang Zhang^a, Xiaochun Yu^a(), Zheng-Jun Wang^a^,^c()

a College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035
b Wenzhou Market Supervision Administration, Wenzhou Quality and Technical Testing Science Research Institute, Wenzhou, Zhejiang 325052
c State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082

Received:2023-12-16 Revised:2024-02-12 Published:2024-03-28
Contact: * E-mail: xiaochunyu@wzu.edu.cn;zj0608wang@163.com
Supported by:
Open Project of State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University(20230767); Basic Scientific Research Projects in Wenzhou City(G20220020)

N-Heterocyclic aromatics are among the most prevalent motifs in natural products, pharmaceuticals, and organic materials. Therefore, the selective functionalization of N-heterocyclic aromatics, represented by the Minisci reaction, has always been a hot topic for chemists. Meanwhile, in recent years, photocatalysis has sparked a new research trend as a green, safe, clean, and renewable catalytic method. Although a review has been conducted on photoinduced Minisci reactions in recent years, the exploration of asymmetric Minisci reactions is limited. The research progress on visible-light photocatalytic asymmetric Minisci reactions in recent years from the classification of free radical precursors and different reaction pathways is summarized. Furthermore, prospects for future development are also discussed.

Key words: asymmetric Minisci reaction, photocatalysis, N-heterocyclic aromatics, free radicals

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Wenya Li, Yu Wang, Jiangqi Chen, Dan Shi, Liang Zhang, Xiaochun Yu, Zheng-Jun Wang. Developments in Visible Light Catalyzed Asymmetric Minisci Reactions[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2110-2123.

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Fig. & Tab. 15

Scheme 1. Schematic diagram of the classic Minsci reaction

Scheme 2. Photoinduced asymmetric Minisci reaction and its radical precursors

Scheme 3. Photoredox/Br?nsted acid co-catalyzed Minisci reaction

Scheme 4. Photocatalytic enantioselective Minisci reactions of diazines and mechanism exploration

Scheme 5. Using N-acetyl-α-amino free radicals in Minisci-type reaction

Scheme 6. Photoinduced non-metallic anion complexes catalyzed Minisci reaction

Scheme 7. Enantioselective hydroalkylation of alkenylpyridines enabled by merging photoactive EDA complexes with chiral bifunctional organocatalysis

Scheme 8. Catalytic asymmetric construction of axially and centrally chiral heterobiaryls by minisci reaction

Scheme 9. Photocatalytic enantioselective Minisci reaction of β-carbolines

Scheme 10. Hydrogen atom transfer-driven enantioselective Minisci reaction of amides

Scheme 11. Photo-promoted copper-catalyzed enantioselective alkylation of azoles

Scheme 12. Visible light-induced direct α-C—H functionalization of alcohols

Scheme 13. Hydrogen atom transfer driven enantioselective Minisci reaction of alcohols

Scheme 14. Asymmetric synthesis of heterocyclic γ-Amino-Acid and diamine derivatives by three-component radical cascade reaction

Scheme 15. Enantioselective chemodivergent three-component radical tandem reactions through asymmetric photoredox catalysis

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可见光催化不对称Minisci反应研究进展

Developments in Visible Light Catalyzed Asymmetric Minisci Reactions

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