洛森重排反应研究进展

doi:10.6023/cjoc202202030

摘要/Abstract

异氰酸酯是一种重要的有机合成中间体, 经霍夫曼重排、柯提斯重排或洛森重排反应等方法制得. 与霍夫曼重排和柯提斯重排相比, 科学家们对反应条件温和、过程安全和试剂毒害性低的洛森重排反应产生了极大的兴趣, 展开了一系列研究和应用. 结合洛森重排反应机理, 对历年来典型的洛森重排反应的研究成果进行了系统性总结, 并对该研究领域的发展前景进行了展望.

关键词: 洛森重排, 异羟肟酸, 异氰酸酯, 合成

Isocyanate is an important intermediate in organic synthesis, which could be prepared via the reaction of Hoffman rearrangement, Curtis rearrangement or Lossen rearrangement. Considering avoiding the hazardous and potentially explosive reagents, chemists have focused on Lossen rearrangement and made the progress and applications of this reaction. The development and applications of the typical reactions of Lossen rearrangement based on its mechanism are systematically summarized. The direction of future research is also prospected.

Key words: Lossen rearrangement, hydroxamic acid, isocyanate, synthesis

引用此文

崔银, 张国富, 丁成荣. 洛森重排反应研究进展[J]. 有机化学, 2022, 42(7): 2015-2027.

Yin Cui, Guofu Zhang, Chengrong Ding. Recent Advances in Lossen Rearrangement[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2015-2027.

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图/表 35

图式1. 经重排反应生成异氰酸酯

Scheme 1. Synthesis of isocyanate via rearrangement

图式2. 洛森重排的起源

Scheme 2. Origin of Lossen rearrangement

图式3. 经典洛森重排反应底物

Scheme 3. Substrates of classical Lossen rearrangement

图式4. 经典洛森重排的反应机理

Scheme 4. Reaction mechanism of classical Lossen rearrangement

图式5. “直接洛森重排”的首次报道

Scheme 5. First report of the “direct Lossen rearrangement”

图式6. 锌催化洛森重排可能的机理

Scheme 6. Plausible mechanism of Zinc-assisted Lossen rearrangement

图式7. 金属催化洛森重排的常规机理

Scheme 7. General mechanism of metal-assisted Lossen rearrangement

图式8. 苯异羟肟酸在铜催化的N-芳基化条件下转化成苯胺

Scheme 8. Conversion of benzohydroxamic acid to aniline under copper-catalyzed N-arylation conditions

图式9. 自催化机制的洛森重排机理

Scheme 9. Self-propagative mechanism for Lossen rearrangement

图式10. 乙酸酐促进的自催化洛森重排

Scheme 10. Acetic anhydride catalyzed self-propagative Lossen rearrangement

图式11. 乙腈促进的自催化洛森重排

Scheme 11. Acetonitrile catalyzed self-propagative Lossen rearrangement

图式12. 羰基二咪唑促进的洛森重排

Scheme 12. CDI-promoted Lossen rearrangement

图式13. TCT促进的洛森重排

Scheme 13. TCT-promoted Lossen rearrangement

图式14. BDMS促进的洛森重排

Scheme 14. BDMS-promoted Lossen rearrangement

图式15. 碳酸二甲酯促进的洛森重排

Scheme 15. DMC-promoted Lossen rearrangement

图式16. 4-NsCl促进的洛森重排

Scheme 16. 4-NsCl-promoted Lossen rearrangement

图式17. 4-NBsOXY促进的洛森重排

Scheme 17. 4-NBsOXY-promoted Lossen rearrangement

图式18. Boc-Oxyma促进的洛森重排

Scheme 18. Boc-Oxyma-promoted Lossen rearrangement

图式19. 4-NBsOXY促进的洛森重排可能的机理

Scheme 19. Plausible mechanism of 4-NBsOXY-promoted Lossen rearrangement

图式20. Boc-Oxyma促进的洛森重排可能的机理

Scheme 20. Plausible mechanism of Boc-Oxyma-promoted Lossen rearrangement

图式21. 硫酰氟促进的洛森重排

Scheme 21. SO2F2-promoted Lossen rearrangement

图式22. 膦酸衍生物的洛森重排

Scheme 22. Lossen rearrangement of phosphonic acid derivatives

图式23. 磺酸衍生物的洛森重排

Scheme 23. Lossen rearrangement of sulfonic acid derivatives

图式24. 罗丹明-异羟肟酸和DCP的荧光显色反应

Scheme 24. Fluorogenic and chromogenic reaction of rhodamine-hydroxamate with DCP

图式25. PTS和DCP的荧光显色反应

Scheme 25. Fluorogenic and chromogenic reaction of PTS with DCP

图式26. 经洛森重排水解致癌的卤代醌

Scheme 26. Hydrolysis of carcinogenic halogenated quinones via Lossen rearrangement

图式27. 经洛森重排合成酚类化合物

Scheme 27. Synthesis of phenols via Lossen rearrangement

图式28. 经洛森重排合成酰胺类化合物

Scheme 28. Synthesis of amides via Lossen rearrangement

图式29. 经洛森重排合成肼类衍生物

Scheme 29. Synthesis of hydrazine derivatives via Lossen rearrangement

图式30. 洛森重排与Heck反应联用

Scheme 30. Combination of Lossen rearrangement and Heck reaction

图式31. 应用氧化酰胺改善C—H键活化性能

Scheme 31. Improving oxidative C—H olefination reactions by using internal oxidants

图式32. 结合洛森重排和C—H键活化合成吲哚和吡咯类化合物

Scheme 32. Synthesis of indole and pyrrole compounds via Lossen rearrangement and C—H bond activation

图式33. 结合洛森重排和C—H键活化构建螺环吲哚酮骨架

Scheme 33. Synthesis of spirooxindole pyrrolones via Lossen rearrangement and C—H bond activation

图式34. 铑催化C—H活化/选择性内酯开环

Scheme 34. Rh(III)-Catalyzed C—H activation/selective lactone ring-opening

图式35. 经洛森重排和C—H键活化将芳基异羟肟酯和炔烃化合物转化为具有喹诺酮结构的氨基酸衍生物

Scheme 35. C—H activation of aryl hydroxamates with acetylene to quinolone-containing amino acid derivatives via the Lossen rearrangement

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