可见光诱导的无过渡金属催化交叉脱氢偶联反应研究进展

doi:10.6023/cjoc201905016

摘要/Abstract

交叉脱氢偶联反应通过两种不同的X-H键直接偶联生成新的化学键，具有优异的步骤经济性和原子经济性.传统交叉脱氢偶联反应通常以过渡金属催化，存在催化剂昂贵及污染严重等问题.可见光诱导电子转移也是实现X-H键直接官能化的有效途径.可见光诱导的无过渡金属催化交叉脱氢偶联反应因具有清洁安全、步骤和原子经济性高等优点从而受到广泛关注.根据成键类型分类，综述了该类反应的研究进展，并对其前景进行了展望.

关键词: 交叉脱氢偶联, 可见光诱导, 无过渡金属, 官能化

The cross dehydrogenation coupling reaction realizes direct coupling of two different X-H bonds to form a new chemical bond, thus featuring excellent step and atom economy. The traditional cross dehydrogenation coupling reaction was usually catalyzed by transition metal, which had the problems of expensive catalyst and serious pollution. Visible light-induced electron transfer is also an effective way to realize direct functionalization of X-H bonds. Visible-light-induced cross dehydrogenation coupling reaction under transition metal-free conditions is widely concerned due to the advantages of cleanliness, safety as well as high step and atom economy. Classified by the type of bonding, the research progress of these reactions is reviewed, and their future outlook is also discussed.

Key words: cross dehydrogenation coupling, visible-light-induced, transition metal-free, functionalization

引用此文

孔瑶蕾, 徐雯秀, 叶飞霞, 翁建全. 可见光诱导的无过渡金属催化交叉脱氢偶联反应研究进展[J]. 有机化学, 2019, 39(11): 3065-3083.

Kong Yaolei, Xu Wenxiu, Ye Feixia, Weng Jianquan. Recent Advances in Visible-Light-Induced Cross Dehydrogenation Coupling Reaction under Transition Metal-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3065-3083.

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图/表 20

图式 1. N-苯基四氢异喹啉和硝基甲烷的交叉脱氢偶联反应机理

Scheme 1. Cross dehydrogenation coupling mechanism of N-phenyltetrahydroisoquinoline and nitromethane

图式 2. N-苯基四氢异喹啉和亲核试剂的交叉脱氢偶联反应机理

Scheme 2. Cross dehydrogenation coupling mechanism of N-phenyltetrahydroisoquinoline and nucleophile

图式 3. N-芳基四氢喹啉和亲核试剂的交叉脱氢偶联反应

Scheme 3. Cross-dehydrogenation coupling reaction of N-aryltetrahydroquinoline and nucleophiles

图式 4. N-苯基四氢异喹啉和2-重氮基乙酸乙酯的交叉脱氢偶联反应机理

Scheme 4. Cross dehydrogenation coupling mechanism of N-phenyltetrahydroisoquinoline and ethyl 2-diazoacetate

图式 5. 可见光诱导下缺电子芳烃和醚的C-H官能化反应

Scheme 5. Visible light-induced C-H functionalization of electron-deficient aromatics and ethers

图式 6. 四氢-β-咔啉和四氢异喹啉的氧化C-H烯化反应

Scheme 6. Oxidative C-H olefination of tetrahydro-β-carbolines and tetrahydroisoquinolines

图式 7. N-芳基四氢异喹啉和咪唑并[1, 2-a]吡啶的交叉脱氢偶联反应机理

Scheme 7. Cross dehydrogenation coupling mechanism of N-aryltetrahydroisoquinoline and imidazo[1, 2-a]pyridine

图式 8. 可见光诱导下甘氨酸衍生物与吲哚的氧化交叉偶联反应

Scheme 8. Visible light-induced oxidative cross-coupling of glycine derivatives with indoles

图式 9. 可见光催化下杂芳烃的Minisci烷基化反应

Scheme 9. Visible light-induced Minisci alkylation of hetero- aromatics

图式 10. 苯甲醛催化下含氮杂环化合物与甲酰胺的交叉脱氢偶联反应

Scheme 10. Cross dehydrocoupling reaction of nitrogen-containing heterocycles and formamide by benzaldehyde catalysis

图式 11. 苯并噻唑和甲酰胺的交叉脱氢偶联反应机理

Scheme 11. Cross dehydrogenation coupling mechanism of benzothiazole and formamide

图式 12. 吩嗪盐催化芳香醛酰胺化的反应机理

Scheme 12. Reaction mechanism of phenazine salt catalyzing amidation of aromatic aldehydes

图式 13. 可见光催化下芳烃分子的内胺化反应

Scheme 13. Visible light-induced intramolecular amination of aromatics

图式 14. 酚和胺的交叉脱氢偶联反应机理

Scheme 14. Cross dehydrogenation coupling reaction mechanism of phenols and amines

图式 15. 喹啉酰胺和咪唑并吡啶的选择性C—H胺化反应

Scheme 15. Selective C—H amination of quinolinamides and imidazopyridines

图式 16. 甘氨酸酯与2, 3-二氢呋喃的交叉脱氢环化反应

Scheme 16. Cross dehydrocyclization reaction of glycine esters with 2, 3-dihydrofuran

图式 17. 甘氨酸酯与α-当归内酯的交叉脱氢环化反应

Scheme 17. Cross dehydrocyclization reaction of glycine esters with α-angelica lactone

图式 18. 二羰基化合物和硫脲的偶联环化反应

Scheme 18. Coupling-cyclization reaction of dicarbonyl compounds with thioureas

图式 19. 分子间脱氢偶联合成二硫化物

Scheme 19. Synthesis of disulfides by intermolecular dehydrocoupling reaction

图式 20. 硫醇和有机磷化合物的交叉脱氢偶联反应机理

Scheme 20. Cross dehydrogenation coupling reaction mechanism of mercaptan and organophosphorus compounds

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