可见光诱导的钯催化Heck反应

doi:10.6023/cjoc202303013

有机化学 ›› 2023, Vol. 43 ›› Issue (9): 3035-3054.DOI: 10.6023/cjoc202303013 上一篇下一篇

综述与进展

可见光诱导的钯催化Heck反应

徐伟^a, 翟宏斌^a^,^b^,^*(), 程斌^a^,^*(), 汪太民^a^,^*()

a 深圳职业技术学院海洋生物医药研究院广州深圳 518055
b 北京大学深圳研究生院化学生物学与生物技术学院化学基因组学重点实验室广州深圳 518055

收稿日期:2023-03-10 修回日期:2023-05-23 发布日期:2023-06-06
基金资助:
广东省教育厅产教融合创新平台(6021210004P); 广东省教育厅创新团队(2021KCXTD069); 深圳职业技术学院博士后启动基金(6021330005K); 深圳市科技创新委员会(JSGG20201103153800002); 深圳市科技创新委员会(GJHZ20200731095412037); 深圳市科技创新委员会(JCYJ20200109141808025)

Visible Light-Induced Pd-Catalyzed Heck Reactions

Wei Xu^a, Hongbin Zhai^a^,^b(), Bin Cheng^a(), Taimin Wang^a()

a Shenzhen Polytechnic, Institute of Marine Biomedicine, Shenzhen, Guangdong 518055
b Peking University Shenzhen Graduate School, State Key Laboratory of Chemical Oncogenomics, Shenzhen, Guangdong 518055

Received:2023-03-10 Revised:2023-05-23 Published:2023-06-06
Contact: * E-mail: zhaihb@pkusz.edu.cn;chengbin@szpt.edu.cn;wangtm@szpt.edu.cn
Supported by:
Marine Medicine Innovation Platform for the Integration of Production and Education of Guangdong Provincial Education Department(6021210004P); Innovation Team of Guangdong Education Department(2021KCXTD069); Post-doctoral Foundation Project of Shenzhen Polytechnic(6021330005K); Shenzhen Science and Technology Innovation Committee(JSGG20201103153800002); Shenzhen Science and Technology Innovation Committee(GJHZ20200731095412037); Shenzhen Science and Technology Innovation Committee(JCYJ20200109141808025)

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摘要/Abstract

Heck反应作为构建C—C键最为强大和实用的合成工具之一, 经过数十年的发展已逐渐趋于成熟, 并在各种功能分子的合成中获得了极为广泛的应用. 近年来, 随着光催化的兴起, 可见光诱导的钯催化Heck反应也随之快速发展起来. 作为一种新颖的C—C键构建策略, 可见光诱导的Heck反应极大地扩展了底物的适用范围, 包括亲核试剂和亲电试剂. 同时, 这种由激发态钯络合物引发, 机理上涉及杂化的自由基-Pd^Ⅰ物种的特殊反应路径也使得可见光诱导的钯催化Heck反应表现出条件温和、官能团兼容性好以及转化多样性等特点, 是对经典Heck反应的极大补充, 在功能分子的合成以及复杂化合物的后期修饰等方面极具应用潜力. 根据反应亲核/亲电试剂种类, 以及串联反应类型, 对可见光诱导的Heck反应进行归类和总结, 并对部分反应机理进行了简要阐述.

关键词: 可见光, 一价钯物种, 自由基, 单电子转移, Heck反应

Heck reaction is regarded as one of the most powerful and practical synthetic tools to construct C—C bonds, and has gained increasingly widespread applications in the synthesis of various functional molecules over the past decades. As an emerging strategy for the formation of C—C bonds, visible light-induced Pd-catalyzed Heck reaction has tremendously extended the scope of substrates, in both aspects of nucleophiles and electrophiles. This unique transformation, triggered by photoexcited Pd⁰ and mechanistically involving hybrid radical-Pd^Ⅰ species, features mild conditions, excellent functional compatibility and transformational diversity, which greatly complements classical Heck reaction catalyzed by ground-state Pd complexes. These advantages will render visible light-induced Heck reaction widespread applications in the synthesis of functional molecules and late-stage modification of structurally complex compounds. According to the species of nucleophiles/ electrophiles and types of cascade reactions, visible light-induced Heck reactions are logically classified, and some of the elusive reaction mechanisms are also illustrated.

Key words: visible light, Pd^Ⅰ species, radical, single electron transfer, Heck reaction

引用此文

徐伟, 翟宏斌, 程斌, 汪太民. 可见光诱导的钯催化Heck反应[J]. 有机化学, 2023, 43(9): 3035-3054.

Wei Xu, Hongbin Zhai, Bin Cheng, Taimin Wang. Visible Light-Induced Pd-Catalyzed Heck Reactions[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3035-3054.

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图/表 35

图1. 经典的Heck与可见光诱导的Heck反应机理比较

Figure 1. Mechanical comparation between classical and visible light-induced Heck reaction

图式1. 一级(二级)碘(或溴)代烷与芳基乙烯的Heck反应

Scheme 1. Heck reaction between primary (or secondary) alkyl bromides or iodides and aryl alkenes

图式2. 各种烷基溴与烯烃的Heck反应

Scheme 2. Heck reaction between various bromoalkanes and alkenes

图式3. 三级碘(或溴)代烷与烯烃的Heck反应

Scheme 3. Heck reaction between tertiary alkyl iodides (or bromides) and alkenes

图式4. 氟代烷基碘与苯乙烯衍生物的Heck反应

Scheme 4. Heck reaction between fluoroalkyl iodides and styrene derivatives

图式5. 溴代糖的Heck反应

Scheme 5. Heck reaction of brominated sugars

图式6. 1,2-自旋中心迁移/Heck反应实现糖的C2-烯基化

Scheme 6. C2-alkenylation of carbohydrates enabled by 1,2-SCS/Heck reaction

图式7. 1,2-自旋中心迁移/Heck反应实现糖的C2-羰甲基化

Scheme 7. C2-ketonylation of carbohydrates enabled by 1,2-SCS/Heck reaction

图式8. 非活化氯代烷的Heck反应

Scheme 8. Heck reaction of unactivated alkyl chlorides

图式9. N-酰氧基邻苯二甲酰亚胺参与的Heck反应

Scheme 9. Heck reaction of N-(acyloxy)phthalimides

图式10. N-酰氧基邻苯二甲酰亚胺参与的Heck反应

Scheme 10. Heck reaction of N-(acyloxy)phthalimides

图式11. 环丁酮肟酯参与的开环/Heck反应

Scheme 11. Ring-opening Heck reaction of cyclobutanone oxime esters

图式12. 重氮化合物或磺酰腙参与的Heck反应

Scheme 12. Heck reaction with diazo compounds or sulfonyl hydrazones

图式13. 钯氢促进的高张力分子的Heck反应

Scheme 13. Palladium hydride-enabled Heck reaction of strained molecules

图式14. 烯醇硅醚或烯胺作为亲核试剂参与的Heck反应

Scheme 14. Heck reaction with silyl enol ethers or enamides as nucleophiles

图式15. 甲醛肟醚参与的Heck反应

Scheme 15. Heck reaction of formaldoximes

图式16. α-酯基腙参与的Heck反应

Scheme 16. Heck reaction of α?ester hydrazones

图式17. 由烷基到烷基的自由基接力Heck反应

Scheme 17. Alkyl-to-alkyl radical relay Heck reaction

图式18. 由芳基到烷基的自由基接力Heck反应

Scheme 18. Aryl-to-alkyl radical relay Heck reaction

图2. Heck/Tsuji-Trost串联反应实现共轭二烯的双官能团化

Figure 2. Difunctionalization of conjugated dienes via tandem Heck/Tsuji-Trost reaction

图式19. Heck/Tsuji-Trost反应实现二烯的1,4-氨烷基化

Scheme 19. 1,4-Aminoalkylation of diene via tandem Heck/Tsuji-Trost reaction

图式20. 三组分的Heck/Tsuji-Trost串联反应

Scheme 20. Three-component tandem Heck/Tsuji-Trost reaction

图式21. Heck/Tsuji-Trost反应实现二烯的1,2-氨烷基化

Scheme 21. 1,2-Aminoalkylation of diene via tandem Heck/Tsuji-Trost reaction

图式22. 溴代二氟乙酰胺参与的二烯1,4-双官能团化

Scheme 22. 1,4-Difunctionalization of dienes with bromodifluoroacetamides

图式23. 原位产生羰自由基参与的Heck/Tsuji-Trost串联反应

Scheme 23. Tandem Heck/Tsuji-Trost reaction of in-situ generated ketyl radicals

图式24. Heck/Heck/Tsuji-Trost一步构建结构复杂化合物

Scheme 24. Construction of structurally complex scaffolds in a single step via tandem Heck/Heck/Tsuji-Trost reaction

图式25. Heck/CO2捕获快速构建2-噁唑啉酮

Scheme 25. Rapid access to 2-oxazolidinones via Heck/CO2 capture

图式26. Heck/CO2捕获快速构建苯并噁嗪酮

Scheme 26. Rapid access to benzoxazinones via Heck/CO2 capture

图式27. Dowd-Beckwith重排/Heck串联反应

Scheme 27. Dowd-Beckwith rearrangement/Heck cascade reaction

图式28. Heck/Heck串联反应

Scheme 28. Cascade Heck reaction

图式29. 氮杂Heck/Heck串联反应

Scheme 29. Tandem aza-Heck/Heck reaction

图式30. Heck/芳环C—H键官能团化串联反应

Scheme 30. Tandem Heck/C—H functionalization of arene

图式31. Heck/芳环C—H键官能团化串联反应

Scheme 31. Tandem Heck/C—H functionalization of arene

图式32. 吲哚去芳构化/Heck反应串联

Scheme 32. Tandem dearomatization of indoles/Heck reaction

图式33. 可见光促进的联烯Heck/分子内氨基化串联反应

Scheme 33. Visible light-enhanced tandem Heck/intramolecular amination of allene

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可见光诱导的钯催化Heck反应

Visible Light-Induced Pd-Catalyzed Heck Reactions

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