P/N-杂配铜(I)光催化剂介导的可见光催化反应进展

doi:10.6023/cjoc202406018

摘要/Abstract

自2008年以来, 可见光驱动的光催化反应成为有机化学和催化化学的研究热点之一. 在众多的光催化反应中, 主流的过渡金属光敏剂主要集中在以钌(II)和铱(III)为代表的贵重金属光催化剂上, 但这类金属光催化剂存在中心金属储量少、价格昂贵及毒性较大等缺点. 近年来, 以丰产金属铜(I)为中心金属的光催化剂被不断开发, 并在光催化反应中获得逐步应用. 特别是基于P/N杂配Cu(I)光催化剂介导的光催化反应受到了化学家的极大关注并迅速发展. 该类金属光催化剂具有中心金属储量丰富、价格低廉和毒性较低的优点, 不仅可以替代钌(II)、铱(III)等贵重金属光催化剂催化常规的光催化反应, 而且还能实现钌(II)、铱(III)等光催化剂所不能完成的光催化反应, 对于高效构建有机分子多样性发挥了重要作用. 根据反应机理的不同, 从单电子转移、铜基光催化剂的双功能催化、双金属协同催化及能量转移四个类型出发, 对P/N杂配Cu(I)光催化剂介导的光催化反应进展进行了综述. 最后对该领域所存在的问题和局限性进行了总结, 并对今后的发展方向作了展望.

关键词: 可见光, P/N-杂配铜(I)光催化剂, 光催化反应, 丰产金属

Visible-light-driven photocatalytic reactions have become one of hot research toptics in organic chemistry and catalytic chemistry since 2008. Among various photocatalytic reactions, the predominant tranistion-metal photocatalysts are those photosensitizers based on noble transition-metals, such as Ru(II) and Ir(III) as the central metal. However, this type of tranisition-metal photocatalysts has several drawbacks associated with their central metals including poor reserves in the earth, high prices and high toxicities. Recently, photocatalysts based on the earth-abundant copper(I) as the central metal have been continuously explored and gradually applied in photocatalytic reactions. In this regard, P/N-heteroleptic Cu(I)-photocatalyst- triggered photocatalytic reactions have specially received great attention and gained rapid development. Such Cu(I)- photocatalysts have advantages of abundant reserves, low prices and low toxicities related to their copper(I) central metal. These photocatalysts not only can replace Ru(II)- and Ir(III)-photocatalyts to trigger conventional photocatalytic reactions, but also can realize some photocatalytic reactions that are hard to be accomplished by Ru(II)- and Ir(III)-based photocatalysts, thus playing an important role in the highly efficient construction of molecular diversities. The recent progress in P/N-heteroleptic Cu(I)-photocatalyst-triggered visible-light-driven photocatalytic reactions is reviewed according to four catagories of different reaction mechanisms, namely, single electron transfer, bifunctional catalysis of Cu(I)-photocatalysts, copper/transition metal synergistic catalysis and energy transfer. At the end of this review, the problems and limitations in this field are summarized, and the future reasearch direction of this field is also prospected.

Key words: visible light, P/N-heteroleptic Cu(I) photocatalyst, photocatalytic reaction, earth-abundant metal

引用此文

周思成, 刘运奎. P/N-杂配铜(I)光催化剂介导的可见光催化反应进展[J]. 有机化学, 2025, 45(5): 1644-1668.

Sicheng Zhou, Yunkui Liu. Recent Progresses in P/N-Heteroleptic Cu(I)-Photocatalyst-Mediated Visible-Light-Driven Photocatalytic Reactions[J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1644-1668.

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图/表 34

图1. 代表性的光催化剂

Figure 1. Representative photocatalysts

图式1. P/N-杂配铜(I)光催化剂的制备及部分化合物库

Scheme 1. Synthesis of P/N heteroleptic Cu(I)-photocatalysts and part of compound library

图式2. P/N杂配铜(I)光催化剂和传统贵金属光催化剂在若干光催化反应中的表现对比

Scheme 2. Performance of P/N-heteroleptic Cu(I)-photocatalysts versus traditional noble-metal based photocatalysts in several photocatalytic reactions

图式3. 单电子转移的两种机理模式

Scheme 3. Two mechanistic modes of single electron transfer

图式4. P/N-杂配铜(I)光催化剂催化的芳卤的硼化反应和磺酰胺的脱砜反应

Scheme 4. Borylation of aryl halides and desulfonation of sulfonamides catalyzed by P/N-heteroleptic Cu(I)-photocatalysts

图式5. 通过P/N杂配Cu(I)光催化剂合成[5]螺烯

Scheme 5. Synthesis of [5]helicene through P/N-heteroleptic Cu(I)-photocatalyst

图式6. P/N杂配Cu(I)光催化剂促进三芳基胺合成咔唑

Scheme 6. P/N heteroleptic Cu(I)-photocatalyst-catalyzed synthesis of carbazoles from triarylamines

图式7. P/N-杂配铜(I)光催化剂催化合成1,3-二酮、烷基溴、环戊烷[b]并呋喃-2-酮及5-苯基-1H-吡咯-2-羧酸甲酯类化合物

Scheme 7. P/N-heteroleptic Cu(I)-photocatalyst-catalyzed synthesis of 1,3-diketones, alkyl bromides, cyclopenta[b]furan-2-ones and methyl 5-phenyl-1H-pyrrole-2-carboxylates

图式8. P/N杂配Cu(I)光催化剂催化的烯烃的氯化三氟甲基化反应

Scheme 8. P/N-heteroleptic Cu(I)-photocatalyst-catalyzed chlo- rotrifluoromethylation of olefins

图式9. P/N杂配铜(I)光催化剂催化N-烷氧基邻苯二甲酰亚胺的选择性C(sp3)—H键功能化反应

Scheme 9. P/N-heteroleptic Cu(I)-photocatalyst-catalyzed chemoselective functionalization of C(sp3)—H bonds of N-alkoxyphtha- limides

图式10. P/N杂配铜(I)光催化剂催化NHPI酯与氮杂芳烃的Minsci自由基偶联反应

Scheme 10. P/N-heteroleptic Cu(I)-photocatalyst-catalyzed Minsci radical coupling reaction between NHPI esters and azaarenes

图式11. P/N杂配Cu(I)光催化剂介导的1,n-烯炔的多米诺自由环化反应

Scheme 11. P/N-heteroleptic Cu(I)-photocatalyst-triggered domino radical cyclization of 1,n-enynes

图式12. P/N杂配Cu(I)光催化剂介导的聚合反应

Scheme 12. P/N-heteroleptic Cu(I)-photocatalyst-triggered polymerization reaction

图式13. P/N杂配Cu(I)光催化剂介导的交叉脱氢偶联反应

Scheme 13. P/N-heteroleptic Cu(I)-photocatalys -catalyzed cross-dehydrogenation-coupling reaction

图式14. P/N杂配Cu(I)光催化剂催化有机卤化物的光还原脱卤反应

Scheme 14. P/N-heteroleptic Cu(I)-photocatalyst catalyzed photoreductive dehalogenation of organic halides

图式15. P/N杂配铜(I)光催化剂催化芳香炔烃与烷基醛的脱氧偶联反应

Scheme 15. P/N-heteroleptic Cu(I)-photocatalyst-catalyzed deoxygenative cross coupling between aromatic alkynes and alkyl aldehydes

图式16. P/N杂配铜(I)光催化剂催化叔胺充当烷基自由基等当体与芳炔的偶联反应

Scheme 16. Cross coupling with aromatic alkynes enabled by P/N-heteroleptic Cu(I)-photocatalyst with tertiary amines acting as alkyl radical equivalents

图式17. P/N杂配铜(I)光催化剂催化的基于α-胺基自由基与烯烃复分解(交换)机制进行的1,7-烯炔的脱亚甲基化自由基环化反应

Scheme 17. Demethylenative radical cyclization of 1,7-enynes enabled by P/N-heterolepitc Cu(I)-photocatalyst based on mechanism of metathesis reaction between α-amino radicals and olefin

图式18. P/N杂配铜(I)光催化剂催化[3＋1]自由基环化合成氮杂环丁烷

Scheme 18. Azetidine synthesis via [3＋1] radical cascade cyclization enabled by P/N-heteroleptic Cu(I)-photocatalysts

图式19. P/N杂配铜(I)光催化剂催化串联1,n-氢转移反应构建环丁硅醚衍生物

Scheme 19. Sequential 1,n-HAT enabling construction of cyclobutoxysilanes catalyzed by P/N-heteroleptic Cu(I)-photocatalysts

图式20. P/N杂配铜(I)光催化剂催化炔烃与B2pin2的自由基硼氢化反应

Scheme 20. P/N-heteroleptic Cu(I)-photocatalyst-catalyzed radical hydroboration of alkynes and B2pin2

图式21. P/N杂配铜(I)光催化剂催化胺基环丙烷和官能化炔烃之间的[3＋2]环化反应

Scheme 21. P/N-heteroleptic Cu(I)-photocatalyst-catalyzed [3＋2] cyclization of aminocyclopropanes and functionalized alkynes

图式22. P/N杂配铜(I)光催化剂双功能催化机理示意图

Scheme 22. Illustration of bifunctional catalytic mechanism of P/N-heteroleptic Cu(I)-photocatalyst

图式23. 双功能铜基光敏剂催化醛(酮)合成频哪醇

Scheme 23. Bifunctional Cu(I)-photosensitizer-catalyzed synthesis of pinacols from aldehydes(ketones)

图式24. 光诱导铜催化NHPI酯与末端炔烃的不对称脱羧炔基化反应

Scheme 24. Photoinduced copper-catalyzed asymmetric decarboxylative alkynylation reaction between NHPI esters and terminal alkynes

图式25. P/N杂配Cu(I)光催化剂双功能催化芳炔和芳基硼酸合成1,2-二酮

Scheme 25. Synthesis of 1,2-diketones from arylynes and arylborates catalyzed by bifunctional P/N-heteroleptic Cu(I)-photocatalysts

图式26. Cu(I)光催化剂与其他过渡金属的双金属协同催化光反应示意图

Scheme 26. Illustration of photocatalytic reactions via dual metallic synergetic catalysis by Cu(I)-photocatalysts and other transition metals

图式27. P/N杂配铜(I)光催化剂和CuBr协同催化仲卤代烷和氨基甲酸酯之间的偶联反应

Scheme 27. Photocatalytic cross-coupling between secondary halides and carbamates enabled by synergetic catalysis of P/N-heteroleptic Cu(I)-photocatalyst and CuBr

图式28. P/N杂配Cu(I)光催化剂和钴络合物双金属协同催化芳炔和芳基硼酸合成1,2-二酮

Scheme 28. Synthesis of 1,2-diketones from arylynes and arylborates via dual metallic synergetic catalysis by Cu(I)-photocatalyst and cobalt complex

图式29. P/N杂配Cu(I)光催化剂和镍络合物双金属协同光催化烷基氯化物还原环化反应

Scheme 29. Photocatalytic reductive cyclization of alkyl chlorides via dual metallic synergetic catalysis by Cu(I)-photocatalyst and nickel complex

图式30. P/N杂配Cu(I)光敏剂催化查尔酮的分子间[2＋2]的光二聚

Scheme 30. [2＋2] photodimerization of chalcones catalyzed by P/N-heteroleptic Cu(I) photosensitizer

图式31. P/N杂配Cu(I)光敏剂催化(E)型-烯烃异构化为(Z)型烯烃

Scheme 31. P/N-heteroleptic Cu(I) photosensitizeer-catalyzed isomerization of (E)-olefins to (Z)-isomers

图式32. P/N杂配铜(I)光敏剂催化能量转移和光氧化还原串联过程合成苯并[b]芴醇

Scheme 32. P/N-heteroleptic Cu(I)-photosensitizer enabling combination of energy-transfer and photoredox catalysis for the synthesis of benzo[b]fluorenols

图式33. 金属有机框架支撑的P/N杂配铜(I)光敏剂催化分子间交叉[2＋2]环加成反应

Scheme 33. Intermolecular crossed [2＋2] cycloaddition reaction catalyzed by a MOF-supported P/N-heteroleptic Cu(I)-photo- sensitizer

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