Visible Light-Induced Pd-Catalyzed Heck Reactions

doi:10.6023/cjoc202303013

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3035-3054.DOI: 10.6023/cjoc202303013 Previous Articles Next Articles

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)

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

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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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Fig. & Tab. 35

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

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

Scheme 2. Heck reaction between various bromoalkanes and alkenes

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

Scheme 4. Heck reaction between fluoroalkyl iodides and styrene derivatives

Scheme 5. Heck reaction of brominated sugars

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

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

Scheme 8. Heck reaction of unactivated alkyl chlorides

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

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

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

Scheme 12. Heck reaction with diazo compounds or sulfonyl hydrazones

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

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

Scheme 15. Heck reaction of formaldoximes

Scheme 16. Heck reaction of α?ester hydrazones

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

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

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

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

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

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

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

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

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

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

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

Scheme 27. Dowd-Beckwith rearrangement/Heck cascade reaction

Scheme 28. Cascade Heck reaction

Scheme 29. Tandem aza-Heck/Heck reaction

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

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

Scheme 32. Tandem dearomatization of indoles/Heck reaction

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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Fig. & Tab. 35

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