联烯胺化合物的区域选择性双官能团化

doi:10.6023/cjoc202309006

摘要/Abstract

联烯胺作为一种富电子联烯类化合物, 由于其具有不同的反应位点和较高的活性, 近年来受到了广泛的关注. 高效可控地实现联烯胺化合物的区域选择性官能团化, 可以成功构建多类有价值的分子骨架. 主要讨论了近几年来在联烯胺化合物的区域选择性双官能团化领域的研究进展, 并详细讨论了多数转化的反应机理.

关键词: 联烯胺, 区域选择性, 双官能团化

As an electron-rich diene compound, N-allenamine has received wide spread attention in recent years due to its different reaction sites and high reactivity. Efficient and controllable regioselective functionalization of N-allenamines can successfully construct functionalized molecules. The research progress in the field of regioselective bifunctionalization of N-allenamines in recent years is mainly discussed, and the reaction mechanisms of most conversions in detail are discussed.

Key words: N-allenamine, regioselectivity, difunctionalization

引用此文

张剑, 梁万洁, 杨艺, 闫法超, 刘会. 联烯胺化合物的区域选择性双官能团化[J]. 有机化学, 2024, 44(2): 335-348.

Jian Zhang, Wanjie Liang, Yi Yang, Fachao Yan, Hui Liu. Regiocontrollable Difunctionalization of N-Allenamines[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 335-348.

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图/表 38

图式1. 联烯胺的区域选择性转化

Scheme 1. Regioselectivity conversion of N-allenamide

图式2. 立体选择性[2＋2]联烯向烯烃和炔的环加成反应

Scheme 2. Stereoselective [2＋2] cycloaddition of allenes toward alkenes and alkynes

图式3. 联烯胺的分子内立体选择性[4＋3]环加成反应

Scheme 3. Stereoselective intramolecular [4＋3] cycloadditions of N-allenamides

图式4. 联烯胺的热分子内[4＋2]环加成反应

Scheme 4. Thermal intramolecular [4＋2] cycloadditions of N- allenamides

图式5. 金催化联烯胺和二烯的不对称分子间[4＋2]环加成反应

Scheme 5. Asymmetric intermolecular[4＋2] cycloadditions of N-allenamides and diene

图式6. 金催化乙烯基吲哚和联烯胺分子间环加成反应

Scheme 6. Gold-catalyzed intermolecular cyclization of ethenyl indole derivatives and N-allenamide

图式7. 3-苯乙烯吲哚与联烯胺分子间[2＋2]与[4＋2]环加成反应

Scheme 7. Intermolecular [2＋2] and [4＋2] cyclization of 3- styrylindoles with N-allenamides

图式8. Au(I)催化联烯胺与α,β-不饱和腙的分子间环加成

Scheme 8. Au(I)-catalyzed cycloaddition of allenamides with α,β-unsaturated hydrazones

图式9. 对映选择性金催化吲哚与联烯胺[2＋2]环加成反应

Scheme 9. Enantioselective [2＋2] cycloaddition between indoles and N-allenamides

图式10. 金催化的区域发散[2＋2＋2]-三氮杂联烯环加成

Scheme 10. Gold-catalyzed regiodivergent [2＋2＋2] cycloadditions of allenes with triazines

图式11. 金催化的[2＋2＋2＋2] 1,3,5-六氢-1,3,5-三嗪与联烯胺的环化反应

Scheme 11. Gold-catalyzed [2＋2＋2＋2] annulation of 1,3,5- hexahydro-1,3,5-triazines with N-allenamides

图式12. 苯乙炔和环戊二烯与联烯胺的[2＋2]和[4＋2]环加成反应

Scheme 12. [2＋2] and [4＋2] cycloadditions of phenylacetylene and cyclopentadiene with N-allenamides

图式13. 喹啉两性离子与联烯胺[5＋2]环加成反应

Scheme 13. [5＋2] cycloaddition of quinolinium zwitterions and N-allenamides

图式14. 联烯和烯基肟醚之间的对映选择性环化

Scheme 14. Annulations between allenes and alkene-tethered oxime ethers

图式15. 4H-呋喃[2-b]吲哚与联烯胺的级联反应

Scheme 15. Cascade reactions of 4H-furo[2-b]indoles with N-allenamides

图式16. 金催化蒽与联烯胺的[4＋2＋2]环加成反应

Scheme 16. Gold-catalyzed [4＋2＋2]-cycloaddition of anthranils with N-allenamides

图式17. 钯催化的联烯胺与活性甲基化合物碳钯化/烯丙基化反应

Scheme 17. Palladium-catalyzed N-allenamide carbopalladation/allylation with active methine compounds

图式18. 镍催化1,2-二烯的氰化酯化反应

Scheme 18. Cyanoesterification of 1,2-dienes catalyzed by nickel

图式19. 镍催化的联烯胺区域选择性和立体选择性芳基化和甲基化

Scheme 19. Nickel-catalyzed arylation and methylation of N- allenamides via coupling reactions

图式20. 联烯胺的分子间碘官能团化

Scheme 20. Intermolecular iodofunctionalization of N-allen- amides

图式21. Lewis酸催化与硅化亲核试剂的亲核加成反应

Scheme 21. Lewis acid-catalyzed nucleophilic addition with silylated nucleophiles

图式22. 金催化联烯胺与乙基苯并碘酮的1,2-氧炔基化反应

Scheme 22. Gold-catalyzed 1,2-oxyalkynylation of N-allena- mides with ethylnylbenziodoxolones

图式23. 铜催化的联烯的碘磺酰化双功能化反应

Scheme 23. Copper-catalyzed difunctionalization of allenes with sulfonyl iodides

图式24. 手性联烯胺与异二烯的立体选择性[4＋2]环加成反应

Scheme 24. Stereoselective [4＋2] cycloaddition reactions of chiral N-allenamides with heterodienes

图式25. 联烯胺衍生酰基离子的酸催化环化反应

Scheme 25. Acid-catalyzed cyclization of acyliminium ions derived from N-allenamides

图式26. 基于N-Boc基团保护的联烯胺环化

Scheme 26. Cyclization of N-Boc-protected N-allenamides

图式27. 3-苯乙烯吲哚与联烯胺分子间[2＋2]与[4＋2]环加成反应

Scheme 27. Intermolecular [2＋2] and [4＋2] cycloadditions of 3-styrylindoles with N-allenamides

图式28. 在联烯胺近端C=C键的高度区域选择性分子间环化

Scheme 28. Intermolecular annulations with N-allenamides at the proximal C=C Bond

图式29. 乙烯基重氮化合物与联烯胺的[3＋2]碳环加成反应

Scheme 29. [3＋2] carbocycloaddition reaction of vinyldiazo compounds and N-allenamides

图式30. 联烯胺-烯分子内[2＋2]环加成反应

Scheme 30. Intramolecular [2＋2] cycloaddition of N-allena- mide

图式31. 金催化的联烯胺不对称分子内环化反应

Scheme 31. Gold-catalyzed asymmetric intramolecular cyclization of N-allenamides

图式32. 铑催化联烯胺[2＋2]环加成反应

Scheme 32. Rhodium-catalyzed [2＋2] cycloaddition of N- allenamide

图式33. 苯并三唑与联烯胺的对映选择性环化反应

Scheme 33. Enantioselective cyclization reaction of benzotriazoles with N-allenamides

图式34. 钯催化联烯胺近端加成反应

Scheme 34. Palladium-catalyzed proximal addition of N-allen- amides

图式35. 铜催化的区域选择性三氟氧甲基化

Scheme 35. Copper-catalyzed regioselective oxytrifluoromethylation

图式36. 联烯胺的无金属C—H功能化反应

Scheme 36. Metal-free C—H functionalization of N-allena- mides

图式37. 金催化的高非对映选择性联烯胺氧化-炔丙基化反应

Scheme 37. Gold-catalyzed highly diastereoselective oxy-pro- pargylamination of N-allenamides

图式38. 光催化联烯胺分子间自由基加成

Scheme 38. Photoredox-catalyzed intermolecular radical addition of N-allenamides

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