碳酸亚乙烯酯参与C—H键活化反应的研究进展

doi:10.6023/cjoc202302009

摘要/Abstract

过渡金属催化导向的C—H键活化反应因具有较高的原子经济性和区域选择性, 为一系列多样性的有机分子的制备提供了一种简便有效的合成渠道. 在众多偶联试剂中, 碳酸亚乙烯酯作为一类新颖、多角色的偶联试剂而被广泛应用于C—H键官能团化反应中. 综述了碳酸亚乙烯酯参与C—H键活化反应的研究进展, 并对其发展前景进行了讨论.

关键词: 碳酸亚乙烯酯, 过渡金属催化, C—H键活化

Transition metal-catalyzed directed C—H bond activation reactions have emerged as a simple and powerful strategy for the construction of multifarious organic molecules due to their high atom-economy and regioselectivity. Among various coupling reagents, vinylene carbonate as a novel and multifunctional coupling reagent has been extensively explored in the transition-metal-catalyzed C—H bond functionalization. In this paper, the recent progress on the application of vinylidene carbonate in C—H bond activation reactions is summarized and the prospect of vinylidene carbonate is discussed.

Key words: vinylene carbonate, transition metal-catalysis, C—H bond activation

引用此文

高晓阳, 翟锐锐, 陈训, 王烁今. 碳酸亚乙烯酯参与C—H键活化反应的研究进展[J]. 有机化学, 2023, 43(9): 3119-3134.

Xiaoyang Gao, Ruirui Zhai, Xun Chen, Shuojin Wang. Recent Progress in C—H Bond Activation Reaction with Vinylene Carbonate[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3119-3134.

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图/表 38

图式1. 碳酸亚乙烯酯参与过渡金属催化C—H键的活化反应

Scheme 1. Transition metal-catalyzed C—H bond activation reaction with vinylene carbonate

图式2. 铑(III)催化苯甲酰胺与碳酸亚乙烯酯的[4+2]环化反应

Scheme 2. Rh(III)-catalyzed [4+2] annulation of benzamides with vinylene carbonate

图式3. 铑(III)催化苯甲酰胺与碳酸亚乙烯酯的[4+2]环化反应机理

Scheme 3. Proposed reaction mechanism for the Rh(III)- catalyzed [4+2] annulation of benzamides with vinylene carbonate

图式4. 铑(III)催化3-羟基苯甲酰胺与碳酸亚乙烯酯的[3+2]环化反应

Scheme 4. Rh(III)-catalyzed [3+2] annulation of 3-hydroxy- benzamides with vinylene carbonate

图式5. 钴(III)催化苯甲酰胺与碳酸亚乙烯酯的[4+2]环化反应

Scheme 5. Co(III)-catalyzed [4+2] cyclization of benzamide with vinylene carbonate

图式6. 8-氧代伪巴马汀和氧巴马汀的全合成

Scheme 6. Total synthesis of 8-oxopseudopalmatine and oxopalmatine

图式7. 苯甲酰胺与碳酸亚乙烯酯环化反应的决速步骤

Scheme 7. Rate-determining step of annulation of benzamides and vinylene carbonate

图式8. 铑(III)和钌(II)催化2-苯基喹唑啉酮与碳酸亚乙烯酯的[4+2]环化反应

Scheme 8. Rh(III)- and Ru(II)-catalyzed [4+2] cyclization of 2-phenylquinazolinone with vinylene carbonate

图式9. 钌(II)催化2-苯基喹唑啉酮与碳酸亚乙烯酯的[4+2]环化反应

Scheme 9. Ru(II)-catalyzed [4+2] cyclization of 2-phenyl- quinazolinone with vinylene carbonate

图式10. 钌(II)催化的喹唑啉酮基导向的(杂)芳烃或烯烃C—H键与碳酸亚乙烯酯的[4+2]环化反应

Scheme 10. Ru(II)-catalyzed quinazolinone-directed (hetero)- arene or alkene C—H bond [4+2] cyclization with vinylene carbonate

图式11. 吴茱萸次碱类天然产物的全合成

Scheme 11. Total synthesis of rutaecarpine natural products

图式12. 铑(III)催化N-芳基亚胺与碳酸亚乙烯酯的[4+2]环化反应

Scheme 12. Rh(III)-catalyzed [4+2] cyclization of N-arylmeth- animines with vinylene carbonate

图式13. 铑(III)催化N-芳基亚胺与碳酸亚乙烯酯[4+2]环化的反应机理

Scheme 13. Proposed reaction mechanism for the Rh(III)-cata- lyzed [4+2] annulation of N-arylmethanimines with vinylene carbonate

图式14. 铑(III)催化亚胺与碳酸亚乙烯酯[4+2]环化反应

Scheme 14. Rh(III)-catalyzed [4+2] cyclization of imines and vinylene carbonate

图式15. 锰(I)催化亚胺与碳酸亚乙烯酯的[4+2]环化反应

Scheme 15. Mn(I)-catalyzed annulation of imines with vinylene carbonate

图式16. 铑(III)催化苯甲酸与碳酸亚乙烯酯的[4+2]环化反应

Scheme 16. Rh(III)-catalyzed [4+2] annulation of benzoic acid with vinylene carbonate

图式17. 铑(III)催化亚磺酰基苯甲酰胺与碳酸亚乙烯酯的 [4+2]环化反应

Scheme 17. Rh(III)-catalyzed [4+2] annulation of sulfonyl benzamide and vinylene carbonate

图式18. 铑(III)催化咪唑与碳酸亚乙烯酯的环化反应

Scheme 18. Rh(III)-catalyzed annulation of imidazopyridine with vinylene carbonate

图式19. 钴(III)催化咪唑并吡啶与碳酸亚乙烯酯的[4+2]环化反应

Scheme 19. Co(III)-catalyzed [4+2] annulation of imidazopyri- dine with vinylene carbonate

图式20. 铑(III)催化3-芳基异恶唑与碳酸亚乙烯酯的[4+2]环化反应

Scheme 20. Rh(III)-catalyzed [4+2] annulation of 3-aryliso- xazoles with vinylene carbonate

图式21. 铑(III)催化N-芳基吲唑酮与碳酸亚乙烯酯的[4+2]环化反应

Scheme 21. Rh(III)-catalyzed [4+2] annulation of N-arylin- dazolones with vinylene carbonate

图式22. 铑(III)催化N-芳基吡唑烷酮与碳酸亚乙烯酯的[4+2]环化反应

Scheme 22. Rh(III)-catalyzed [4+2] annulation of N-arylpyra- zolidinone with vinylene carbonate

图式23. 铑(III)催化烯胺酮与碳酸亚乙烯酯的[4+2]环化反应

Scheme 23. Rh(III)-catalyzed [4+2] annulation of enaminones with vinylene carbonate

图式24. 钌(II)催化N-苯基酰胺与碳酸亚乙烯酯的[3+2]环化反应

Scheme 24. Ru(II)-catalyzed [3+2] cyclization of N-phenyl- pyranamide with vinylene carbonate

图式25. 铑(III)催化2-吡咯苯胺与碳酸亚乙烯酯的[5+1]环化反应

Scheme 25. Rh(III)-catalyzed [5+1] annulation of 2-pyrrolyl- aniline with vinylene carbonate

图式26. 铑(III)催化2-吲哚苯胺与碳酸亚乙烯酯的[5+1]环化反应

Scheme 26. Rh(III)-catalyzed [5+1] annulation of 2-indolylaniline with vinylene carbonate

图式27. 铑(III)催化偶氮苯与碳酸亚乙烯酯的[4+1]或[4+2]环化反应

Scheme 27. Rh(III)-catalyzed [4+1] or [4+2] annulation of azobenzenes with vinylene carbonate

图式28. 铑(III)催化偶氮苯与碳酸亚乙烯酯的[4+1]环化反应

Scheme 28. Rh(III)-catalyzed [4+1] annulation of azobenzenes with vinylene carbonate

图式29. 铑(III)催化亚胺与碳酸亚乙烯酯的[5+1]环化反应

Scheme 29. Rh(III)-catalyzed [5+1] annulation of imines with vinylene carbonate

图式30. 铑(III)催化苯胺与碳酸亚乙烯酯的[3+2+1]环化反应

Scheme 30. Rh(III)-catalyzed [3+2+1] annulation of phenylamine with vinylene carbonate

图式31. 苯并喹啉的合成应用

Scheme 31. Synthetic applications of benzoquinoline

图式32. 铑(III)催化偶氮苯与碳酸亚乙烯酯的串联环化反应

Scheme 32. Rh(III)-catalyzed cascade annulation of azobenzenes with vinylene carbonate

图式33. 铑(III)催化偶氮苯与碳酸亚乙烯酯串联环化的反应机理

Scheme 33. Proposed reaction mechanism for the Rh(III)-catalyzed cascade annulation of azobenzenes with vinylene carbonate

图式34. 铑(III)催化N-芳基吡唑与碳酸亚乙烯酯的酰甲基化反应

Scheme 34. Rh(III)-catalyzed acylmethylation of N-arylpyra- zole with vinylene carbonate

图式35. 铑(III)催化N-芳基吡唑与碳酸亚乙烯酯的酰甲基化的反应机理

Scheme 35. Proposed reaction mechanism for Rh(III)-catalyzed acylmethylation of N-arylpyrazole with vinylene carbonate

图式36. 铑(III)催化N-嘧啶吲哚和N-嘧啶二氢吲哚与碳酸亚乙烯酯的酰甲基化反应

Scheme 36. Rh(III)-catalyzed acylmethylation of N-pyrimi- dylindol and N-pyrimidylindoline with vinylene carbonate

图式37. 铑(III)催化N-嘧啶吲哚与碳酸亚乙烯酯的酰甲基化反应

Scheme 37. Rh(III)-catalyzed acylmethylation of N-pyrimi- dylindol with vinylene carbonate

图式38. 钌(II)催化N-嘧啶二氢吲哚与碳酸亚乙烯酯的酰甲基化与缩醛化反应

Scheme 38. Ru(II)-catalyzed acylmethylation and acetalization of N-pyrimidylindoline with vinylene carbonate

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