氧气为唯一氧化剂的交叉脱氢偶联反应研究进展

doi:10.6023/cjoc202007007

摘要/Abstract

脱氢偶联反应是最有效、最直接的构建C—C键或C—杂键的一种方法. 但是目前大多数脱氢偶联反应需要使用化学计量的有毒氧化剂, 如PhI(OAc)₂、苯醌、Cu(II)盐、有机过氧酸或Ag(I)盐等. 氧气廉价易得, 作为脱氢偶联反应中的唯一氧化剂, 副产物只有水, 不会产生其他有毒副产物, 是绿色环境友好的方法. 根据催化剂的分类, 综述了氧气作为唯一氧化剂的交叉脱氢偶联反应研究进展.

关键词: 交叉脱氢偶联, 氧气, 唯一氧化剂

Cross-dehydrogenative-coupling (CDC) reactions have emerged as one of the most efficient and straightforward methods for the formation of C—C bonds or C-heteroatom bonds. However, most CDC reactions require hazardous and stoichiometric oxidants, such as PhI(OAc)₂, benzoquinone, copper(II) salts, organic peroxide acid and silver(I) salts. A green and environmentary benign approach is using molecular oxygen (O₂) as oxidant in the reactions, which usually form water as by-product. According to the classification of catalysts, the research progress of cross dehydrogenation coupling reaction with oxygen as the only oxidant is reviewed.

Key words: cross-dehydrogenative-coupling, molecular oxygen, oxidant

引用此文

庄伟辉, 张晓凤, 黄秋锋. 氧气为唯一氧化剂的交叉脱氢偶联反应研究进展[J]. 有机化学, 2021, 41(2): 529-542.

Weihui Zhuang, Xiaofeng Zhang, Qiufeng Huang. Recent Advances in Cross-Dehydrogenative-Coupling Reactions Using Molecular Oxygen as the Sole Oxidant[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 529-542.

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图/表 12

图式1. 氧气为唯一氧化剂的交叉脱氢偶联反应

Scheme 1. Cross-dehydrogenative-coupling reactions using molecular oxygen as the sole oxidant

图式2. 氧气作为氧化剂的钯(II)催化脱氢偶联反应的可能机理

Scheme 2. Proposed mechanism of PdII-catalyzed cross-dehydrogenative-coupling using O2 as the oxidant

图式3. 钯催化缺电子芳烃的烯烃化反应

Scheme 3. Pd(II)-catalyzed olefination of electron-deficient arenes

图式4. MPAA促进的钯催化缺电子芳烃烯烃化反应

Scheme 4. Mono-N-protected amino acid ligands accelerated palladium-catalyzed olefination of electron-deficient (hetero)arenes

图式5. 氧气为唯一氧化剂的钯催化多氟芳烃的烯烃化和芳烃化

Scheme 5. Palladium-catalyzed olefination and arylation of polyfluoroarenes using molecular oxygen as the sole oxidant

图式6. 氧气作为唯一氧化剂的钯催化尿嘧啶和咖啡因C—H直接烯烃化反应

Scheme 6. Palladium-catalyzed C—H olefination of uracils and caffeines using molecular oxygen as the sole oxidant

图式7. 氧气作为唯一氧化剂的钯催化尿嘧啶和咖啡因C—H直接芳基化反应

Scheme 7. Palladium-catalyzed C—H arylation of uracils and caffeines using molecular oxygen as the sole oxidant

图式8. 钯催化碳碳叁键的双烯烃化反应

Scheme 8. Palladium-catalyzed bisolefination of C≡C triple bonds

图式9. 铁催化二芳基胺的氧化C—C和N—N偶联反应

Scheme 9. Iron-catalyzed oxidative C—C and N—N coupling of diarylamines

图式10. 空气气氛中铜催化胺和磷酸酯的氧化偶联反应

Scheme 10. Copper-catalyzed aerobic oxidative coupling of amines and phosphonates

图式11. 介孔三氧化二锰催化苯胺的氧化偶联反应

Scheme 11. Mesoporous manganese oxide catalyzed oxidative coupling of anilines

图式12. 无催化剂的呫吨化合物与苯硫酚的脱氢偶联反应

Scheme 12. Catalyst-free cross-dehydrogenative coupling between xanthene derivatives and thiophenols

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