炔酰胺合成方法研究进展

doi:10.6023/cjoc202107051

摘要/Abstract

炔酰胺是一类氮原子上连有吸电子基团的特殊炔胺. 吸电子基团的引入使炔酰胺的稳定性和反应活性达到较好的平衡, 从而赋予炔酰胺丰富多样的反应性能. 近二十年炔酰胺化学发展迅速, 其合成方法已引起广泛关注. 在此背景下, 综述了炔酰胺合成方法的研究进展. 根据使用主要原料的结构, 分别从以卤代烯酰胺、炔烃以及其衍生物和卤代烯烃为关键原料的合成方法进行了阐述, 并对代表性反应机理进行了讨论.

关键词: 炔酰胺, 吸电子基团, 内炔酰胺, 端炔酰胺

Ynamides are a class of special ynamines bearing an electron-withdrawing group on the nitrogen atom. The electron-withdrawing group endows ynamides an optimal balance between the stability and activity, and thus enabling ynamides to be versatile synthons widely used in organic synthetic chemistry. The ynamide chemistry has witnessed a rapid development over the past two decades. As a consequence, its synthetic methods have attracted widespread attention. In this context, the recent advances in the synthesis of ynamides are reviewed herein. According to the structure of the main starting materials, the contents are classified as the synthesis with haloenamides, alkynes or its derivatives, and dihalo-substituted alkenes. The representative mechanisms are also discussed.

Key words: ynamide, electron-withdrawing group, internal ynamide, terminal ynamide

引用此文

赵永丽, 涂永良, 蔡明中, 赵军锋. 炔酰胺合成方法研究进展[J]. 有机化学, 2022, 42(1): 85-99.

Yongli Zhao, Yongliang Tu, Mingzhong Cai, Junfeng Zhao. Recent Advances in the Synthesis of Ynamides[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 85-99.

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图/表 50

图式1. 炔胺的首次合成

Scheme 1. The first synthesis of ynamine

图式2. 炔酰胺的结构

Scheme 2. Structure of ynamides

图式3. 炔酰胺的首次合成

Scheme 3. The first synthesis of ynamide

图式4. 端炔酰胺的首次合成

Scheme 4. The first synthesis of terminal ynamides

图式5. 消除反应合成炔酰胺

Scheme 5. Synthesis of ynamides via elimination reaction

图式6. 以甲酰胺为原料合成炔酰胺

Scheme 6. Synthesis of ynamides with formamides

图式7. 三氯乙烯为原料合成炔酰胺

Scheme 7. Synthesis of ynamides with trichloroethene

图式8. Suzuki-Miyaura偶联反应合成炔酰胺

Scheme 8. Synthesis of ynamides by Suzuki-Miyaura coupling

图式9. 炔碘盐为原料合成炔酰胺

Scheme 9. Synthesis of ynamides with alkynyl iodonium salts

图式10. 炔碘盐合成炔酰胺以及其可能反应机理

Scheme 10. Synthesis of ynamides with alkynyl iodonium salt and the possible mechanism

图式11. 高度官能团化的炔酰胺合成

Scheme 11. Synthesis of highly functionalized ynamides

图式12. 含有炔基的炔酰胺合成

Scheme 12. Synthesis of ynamides containing an alkynyl group

图式13. 手性炔酰胺的首次合成

Scheme 13. The first synthesis of chiral ynamides

图式14. 手性α-支链的炔酰胺合成

Scheme 14. Synthesis of chiral α-branched ynamides

图式15. 无过渡金属合成炔酰胺

Scheme 15. Metal-free synthesis of ynamides

图式16. 醋酸碘苯作为氧化剂合成炔酰胺

Scheme 16. Synthesis of ynamides with PIDA as oxidant

图式17. EBX-乙腈络合物作为原料合成炔酰胺

Scheme 17. Synthesis of ynamides with EBX-MeCN complex

图式18. 高价炔基碘为原料合成炔酰胺以及亮氨酸衍生炔酰胺的应用

Scheme 18. Synthesis of ynamides with hypervalent alkynyl iodine reagents and application of leucine-derived ynamide

图式19. 铜催化首次合成内炔酰胺以及可能反应机理

Scheme 19. The first synthesis of internal ynamides by copper catalysis and proposed mechanism

图式20. 铜介导的炔酰胺合成

Scheme 20. Cu-mediated synthesis of ynamides

图式21. 铜-沸石(USY)催化制备内炔酰胺

Scheme 21. Synthesis of ynamides by copper zeolite (USY) catalysis

图式22. 首次使用铁催化剂合成内炔酰胺

Scheme 22. The first synthesis of ynamide by Fe catalysis

图式23. APGS-550-M催化合成炔酰胺

Scheme 23. Synthesis of ynamides by APGS-550-M catalysis

图式24. N-磷酰基的炔酰胺合成

Scheme 24. Synthesis of N-phosphoryl ynamides

图式25. N-炔基亚砜亚胺合成

Scheme 25. Synthesis of N-alkynyl sulfoximines

图式26. S-全氟炔基亚砜亚胺合成

Scheme 26. Synthesis of S-perfluoro alkynyl sulfoximines

图式27. CuCN催化噁唑烷酮和氨基甲酸酯类炔酰胺合成

Scheme 27. Synthesis of ynamides containing oxazolidinone or carbamate by CuCN catalysis

图式28. CuI 催化亚磺酰胺的N-炔基化反应

Scheme 28. CuI catalyzed N-alkynylation of sulphonamides

图式29. 铜介导的氨基甲酸酯的N-炔基化反应

Scheme 29. Copper-mediated N-alkynylation of carbamates

图式30. 铜盐和1,10-菲罗啉体系下合成炔酰胺

Scheme 30. Synthesis of ynamides with the combination of Cu-salt and 1,10-phen

图式31. CuSO4催化多炔酰胺合成

Scheme 31. Synthesis of multi-ynamides by CuSO4 catalysis

图式32. 丙烯酸的氧化氨化反应以及可能反应机理

Scheme 32. (a) Oxidative amidation and (b) proposed mechanism of propiolic acids

图式33. 氧化脱羧偶联合成N-炔基亚砜亚胺

Scheme 33. Synthesis of N-alkynyl sulfoximines by oxidative decarboxylation coupling

图式34. 炔基硼试剂和酰胺合成炔酰胺

Scheme 34. Synthesis of ynamides with alkynylboron reagents and amides

图式35. 炔基铜试剂发生氧化偶联反应合成炔酰胺

Scheme 35. Synthesis of ynamides by oxidative coupling with alkynylcopper reagents

图式36. N-炔基酰亚胺的首次合成

Scheme 36. The first synthesis of N-alkynyl imides

图式37. 过渡金属催化合成炔酰胺

Scheme 37. Synthesis of ynamides by transition metal catalysis

图式38. 炔烃的氧化胺化反应合成炔酰胺

Scheme 38. Synthesis of ynamides by oxidative amidation of alkynes

图式39. 氢氧化铜催化氧化偶联反应合成炔酰胺

Scheme 39. Synthesis of ynamides by oxidative cross-coupling with copper hydroxide

图式40. (a) 氧化铜介导合成炔酰胺以及(b)可能反应机理

Scheme 40. (a) Synthesis of ynamides by CuO mediated oxidative coupling and (b) proposed mechanism

图式41. 炔酰肼的合成

Scheme 41. Synthesis of ynehydrazides

图式42. 氧化偶联反应合成N-炔基亚砜亚胺

Scheme 42. Synthesis of N-alkynyl sulfoximines by oxidative coupling of alkynes

图式43. 以1,1-二溴烯烃为原料合成炔酰胺

Scheme 43. Synthesis of ynamides with 1,1-dibromo-1-alkenes

图式44. 可能反应机理

Scheme 44. Proposed mechanism

图式45. 选择性生成炔酰胺和双烯酰胺

Scheme 45. Selective synthesis of ynamides and 1,1-dienamides

图式46. 咪唑或吡唑类炔酰胺的合成

Scheme 46. Synthesis of ynamides with imidazoles and pyrazoles

图式47. 以1,2-二溴烯烃为原料合成炔酰胺

Scheme 47. Synthesis of ynamides with 1,2-dibromo-1-styrenes

图式48. 2-溴-1-碘烯烃为原料合成炔酰胺

Scheme 48. Synthesis of ynamides with 2-bromo-1-iodoalkenes

图式49. 双氮炔酰胺的合成

Scheme 49. Synthesis of ynediamides

图式50. 一步法从1,1-或者1,2-二氯烯烃合成炔酰胺

Scheme 50. One step synthesis of ynamides with 1,1- or 1,2- dichloroalkenes

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