可见光催化不对称Minisci反应研究进展

doi:10.6023/cjoc202312016

摘要/Abstract

氮杂芳烃是诸多天然产物、药物和有机材料中常见的结构单元之一, 因此以Minisci反应为代表的对氮杂芳烃进行选择性官能团化修饰一直以来是化学家们的关注热点. 同时, 近年来光催化作为一种绿色安全、洁净环保和可再生的催化方式掀起了新的研究热潮. 尽管近年来光催化Minisci反应已经有相关综述报道, 但是对于不对称Minisci反应却一直鲜有涉猎. 将从自由基前驱体的分类、不同的反应途径等方面概述近年来可见光催化不对称Minisci反应的研究进展, 同时也对今后其发展方向进行了展望.

关键词: 不对称Minisci反应, 光催化, 含氮芳环, 自由基

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

引用此文

李文雅, 王煜, 陈江琦, 史丹, 张良, 余小春, 王正军. 可见光催化不对称Minisci反应研究进展[J]. 有机化学, 2024, 44(7): 2110-2123.

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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图/表 15

图式1. 经典的Minsci反应示意图

Scheme 1. Schematic diagram of the classic Minsci reaction

图式2. 不对称光催化Minisci反应及其自由基前驱体

Scheme 2. Photoinduced asymmetric Minisci reaction and its radical precursors

图式3. 光诱导和Br?nsted酸协同催化的Minisci反应

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

图式4. 光催化二嗪类化合物的对映选择性Minisci反应及其机理研究

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

图式5. N-乙酰基-α-氨基酸自由基参与的Minisci反应

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

图式6. 光诱导非金属阴离子复合物催化的Minisci反应

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

图式7. 手性双官能团催化光致EDA配合物引发的烯基吡啶对映选择性加氢烷基化

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

图式8. 用Minisci反应催化不对称构造轴向和中心手性杂联芳基

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

图式9. β-咔啉的光催化对映选择性Minisci反应

Scheme 9. Photocatalytic enantioselective Minisci reaction of β-carbolines

图式10. 氢原子转移驱动的酰胺类对映选择性Minisci反应

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

图式11. 光催化铜催化偶氮对映选择性烷基化反应

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

图式12. 可见光诱导的醇类直接α-C—H功能化

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

图式13. 氢原子转移驱动的醇的对映选择性Minisci反应

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

图式14. 三组分自由基级联反应合成不对称γ-氨基酸和二胺类杂环衍生物

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

图式15. 通过不对称光氧化还原催化的对映选择性化学发散三组分自由基串联反应

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

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