过渡金属催化的异腈插入反应研究进展

doi:10.6023/cjoc202204007

摘要/Abstract

作为一类含(NC)官能团的高活性有机小分子, 异腈在有机合成、材料化学、配位化学等领域有着非常广泛的应用. 近年来, 过渡金属催化的异腈插入反应由于具有操作简便、成键高效、反应选择性好等优点, 引起了化学家们的关注, 并且通过该类型反应成功构建了一系列十分有用的链状或环状化合物, 例如官能化的酮、酰胺、氮杂环化合物等. 为了更及时地了解该领域的研究进展, 根据金属类别的不同, 对2017至2021年过渡金属催化的异腈插入反应进行了概括和总结, 并对该领域的发展前景进行了展望.

关键词: 过渡金属催化, 异腈, 插入反应, 氮杂环化合物

As a class of small organic molecules containing (NC) functional groups with high activity, isocyanide has been widely employed in organic synthesis, materials science, as well as coordination chemistry. In recent years, the transition metal-catalyzed isocyanide insertion reactions have attracted much attention due to the convenient and simple operations, the efficiency in the formation of diverse new bonds and good reaction selectivity. A series of highly useful chain or cyclic compounds have been successfully constructed using this strategy, such as functionalized ketones, amides, nitrogen heterocyclic compounds, etc. To study the most recent progress, the advances in transition metal-catalyzed isocyanide insertion reactions since 2017 to 2021 are briefly summarized according to different metal categories, and the future development has also been prospected in this review.

Key words: transition metal-catalysis, isocyanide, insertion reactions, nitrogen heterocyclic compounds

引用此文

高秋珊, 李蒙, 伍婉卿. 过渡金属催化的异腈插入反应研究进展[J]. 有机化学, 2022, 42(9): 2659-2681.

Qiushan Gao, Meng Li, Wanqing Wu. Recent Advances in Transition Metal-Catalyzed Isocyanide Insertion Reactions[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2659-2681.

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图/表 64

图式1. 钯催化多取代3-氨基吡咯的合成

Scheme 1. Synthesis of polysubstituted 3-amino pyrroles under palladium catalytic system

图式2. 钯催化偕二溴烯烃和异腈的反应

Scheme 2. Palladium-catalyzed reaction of gem-dibromoalkenes and isocyanides

图式3. 钯催化卤苯、异腈和有机锌试剂的反应

Scheme 3. Palladium-catalyzed reaction of aromatic halides, isocyanides and organozinc reagents

图式4. 钯催化二酮亚胺化合物和N-酰基邻氨基苯甲酰胺衍生物的合成

Scheme 4. Synthesis of diketimine compounds and N-acyl anthranilamide derivatives under palladium-catalyzed system

图式5. 钯催化邻溴苯胺、异腈和CO2的反应

Scheme 5. Palladium-catalyzed reaction of o-bromoanilines, isocyanides and carbon dioxide

图式6. 钯催化邻苯二甲酰亚胺衍生物和1H-茚类化合物的合成

Scheme 6. Synthesis of phthalimide derivatives and 1H-indenes under palladium catalytic system

图式7. 钯催化喹啉并环衍生物的合成

Scheme 7. Synthesis of quinoline derivatives under palladium catalytic system

图式8. 钯催化异吲哚酮类化合物的合成

Scheme 8. Synthesis of isoindolones under palladium-catalyzed system

图式9. 钯催化内炔和异腈的反应

Scheme 9. Palladium-catalyzed reaction of internal alkynes and isocyanides

图式10. 钯催化邻溴苯甲醛和异腈的反应

Scheme 10. Palladium-catalyzed reaction of o-bromobenzalde- hydes and isocyanides

图式11. 钯催化官能化异腈和芳基碘的反应

Scheme 11. Palladium-catalyzed reaction of functionalized isocyanides and iodobenzenes

图式12. 钯催化含菲啶和咔唑结构的杂环化合物的合成

Scheme 12. Synthesis of heterocyclic structures containing both phenanthridine and carbazole scaffolds under palladium catalytic system

图式13. 钯催化官能化异腈和芳基卤化物的反应

Scheme 13. Palladium-catalyzed reaction of functionalized isocyanides and aryl halides

图式14. 钯催化轴手性2-芳基喹唑啉酮衍生物的合成

Scheme 14. Synthesis of axially chiral 2-arylquinazolinone derivatives under palladium-catalyzed system

图式15. 钯催化含三氟(或二氟)甲基手性中心的1H-异吲哚衍生物的合成

Scheme 15. Synthesis of 1H-isoindoles with trifluoro (or difluoro) methyl chiral center under palladium catalytic system

图式16. 钯催化五到七环状酮亚胺取代的乙酰胺衍生物的合成

Scheme 16. Synthesis of acetamides derivatives substituted with five- to seven-membered cyclic ketoimines under palladium catalytic system

图式17. 钯催化炔丙基碳酸酯和异腈的反应

Scheme 17. Palladium-catalyzed reaction of propargyl carbonates and isocyanides

图式18. 钯催化邻炔基烯丙基醚和异腈的反应

Scheme 18. Palladium-catalyzed reaction of o-alkynyl allyl ethers and isocyanides

图式19. 钯催化多取代噻吩衍生物的合成

Scheme 19. Synthesis of polysubstituted thiophene derivatives under palladium catalytic system

图式20. 钯催化杂芳基硫醚和异腈的反应

Scheme 20. Palladium-catalyzed reaction of heteroaryl sulfides and isocyanides

图式21. 钯催化内炔、异腈和二硫化物的反应

Scheme 21. Palladium-catalyzed reaction of internal alkynes, isocyanides and disulfide

图式22. 钯催化四芳基铅和异腈的反应

Scheme 22. Palladium-catalyzed reaction of tetraarylleads and isocyanides

图式23. 钯或铑催化三芳基铋和异腈的反应

Scheme 23. Palladium or rhodium catalyzed reaction of triarylbismuthines and isocyanides

图式24. 钯催化二芳基酮或芳基酰胺的合成

Scheme 24. Synthesis of diaryl ketones or aryl amides under palladium-catalyzed system

图式25. 钯催化芳基/烯基羧酸的合成

Scheme 25. Synthesis of aryl/alkenyl carboxylic acids under palladium-catalyzed system

图式26. 钯催化芳基硼酸、异腈和邻氨基苯甲酰胺的反应

Scheme 26. Palladium-catalyzed reaction of arylboronic acids, isocyanides and anthranilamides

图式27. 钯催化炔烃、异腈和羧酸的反应

Scheme 27. Palladium-catalyzed reaction of alkynes, isocyanides and carboxylic acids

图式28. 钯催化烯酰胺和异腈的反应

Scheme 28. Palladium-catalyzed reaction of enamides and isocyanides

图式29. 钯催化吡咯并[2,1-c][1,4]苯并噁嗪和吡咯并[1,2-a]喹喔啉衍生物的合成

Scheme 29. Synthesis of pyrrolo[2,1-c][1,4]benzoxazine and pyrrolo[1,2-a]quinoxaline derivatives under palladium catalytic system

图式30. 钯催化多取代2-氨基喹啉及其衍生物的合成

Scheme 30. Synthesis of polysubstituted 2-aminoquinolines and their derivatives under palladium catalytic system

图式31. 钯催化炔亚胺和异腈的反应

Scheme 31. Palladium-catalyzed reaction of alkynyl imines and isocyanides

图式32. 钯催化3-芳基异噁唑-5(4H)-酮和异腈的反应

Scheme 32. Palladium-catalyzed reaction of 3-arylisoxazole- 5(4H)-ones and isocyanides

图式33. 钯催化2,3-双取代吲哚类化合物的合成

Scheme 33. Synthesis of 2,3-disubstituted indoles under palladium-catalyzed system

图式34. 钯催化芳基硫酯和异腈的反应

Scheme 34. Palladium-catalyzed reaction of aryl thioesters and isocyanides

图式35. 钯催化端炔、异腈和羧酸钠的反应

Scheme 35. Palladium-catalyzed reaction of terminal alkynes, isocyanides and sodium carboxylates

图式36. 钯催化胺、异腈和炔卤的反应

Scheme 36. Palladium-catalyzed reaction of amines, isocyanides and alkyne halides

图式37. 钯催化丙炔酸和异腈的反应

Scheme 37. Palladium-catalyzed reaction of alkynyl carboxylic acids and isocyanides

图式38. 钯催化N-酰基-邻炔基苯胺和异腈的反应

Scheme 38. Palladium-catalyzed reaction of isocyanides and N- acy-o-alkynylanilines

图式39. 钯催化偕胺肟和异腈的反应

Scheme 39. Palladium-catalyzed reaction of amidoximes and isocyanides

图式40. 钯催化异噁唑酮和异腈的反应

Scheme 40. Palladium-catalyzed reaction of isoxazolones and isocyanides

图式41. 钯催化芳基肟或肟酯和异腈的反应

Scheme 41. Palladium-catalyzed reaction of aryl oximes or oxime esters and isocyanides

图式42. 钯催化胺肟、异腈和伯胺的反应

Scheme 42. Palladium-catalyzed reaction of amidoximes, isocyanides and primary amines

图式43. 钯催化2-酰基苯胺衍生的N-甲苯磺酰腙和异腈的反应

Scheme 43. Palladium-catalyzed reaction of N-tosylhydrazones derived from 2-acylanilines and isocyanides

图式44. 钯催化烯酮亚胺类化合物的合成

Scheme 44. Synthesis of enoneimines under palladium-catalyzed system

图式45. 钯催化喹唑啉-4(3H)-酮类衍生物和四取代咪唑酮类衍生物的合成

Scheme 45. Synthesis of quinazolin-4(3H)-one derivatives and tetra-substituted imidazolone derivatives under palladium-catalyzed system

图式46. 镍催化硫脲和异腈的反应机理

Scheme 46. Nickel-catalyzed reaction mechanism for thioureas and isocyanides

图式47. 镍催化N-尿嘧啶脒和异腈的反应

Scheme 47. Nickel-catalyzed reaction of N-uracil amidines and isocyanides

图式48. 镍催化烯丙基醋酸酯、异腈和烷基锌试剂的反应

Scheme 48. Nickel-catalyzed reaction of allyl acetates, isocynides and alkyl zinc reagents

图式49. 镍催化烷基碘化合物和异腈的反应

Scheme 49. Nickel-catalyzed reaction of alkyl iodides and isocyanides

图式50. 镍催化苄氯和异腈的反应

Scheme 50. Nickel-catalyzed reaction of secondary benzyl chlorides and isocyanides

图式51. 钴催化苯并[d]咪唑胍和异腈的反应

Scheme 51. Cobalt catalyzed reaction of benzo[d]imidazo- guanidines and isocyanides

图式52. 钴催化芳基酰胺和异腈的反应

Scheme 52. Cobalt-catalyzed reaction of arylamides and isocyanides

图式53. 钴催化磺酰叠氮化合物、异腈和不同亲核试剂的反应

Scheme 53. Cobalt-catalyzed reaction of sulfonyl azide, isocyanides and different nucleophiles

图式54. 钴催化邻异氰基苯甲腈、胺和磺酰叠氮化合物的反应

Scheme 54. Cobalt-catalyzed reaction of o-isocyanobenzoni- triles, amides and sulfonyl azides

图式55. 钴催化色氨酸衍生的异腈和磺酰叠氮化合物的反应

Scheme 55. Cobalt-catalyzed reaction of tryptophan-derived isocyanides and sulfonyl azides

图式56. 钴催化重氮酸酯、异腈和胺的反应

Scheme 56. Cobalt-catalyzed reaction of diazoates, isocyanides and amines

图式57. 银催化下α-异氰基乙酸甲酯和伯胺的反应

Scheme 57. Silver-catalyzed reaction of methyl α-isocyano- acetate and primary amines

图式58. 银催化异噁唑-5-酮和异腈的反应

Scheme 58. Silver-catalyzed reaction of isoxazol-5-ones and isocyanides

图式59. 银催化下苯并[b]芴衍生物的合成

Scheme 59. Synthesis of benzo[b]fluorene derivatives under silver-catalyzed system

图式60. 银催化重氮乙烷、2-异氰基苯甲醛和胺的反应

Scheme 60. Silver-catalyzed reaction of diazoethanes, 2-iso- cyanobenzaldehydes and amines

图式61. 铑催化异腈参与的偶联反应

Scheme 61. Rhodium-catalyzed coupling reaction involving isocyanides

图式62. 铑催化叠氮化合物、异腈和醇的反应

Scheme 62. Rhodium-catalyzed reaction of azides, isocyanides and alcohols

图式63. 铜催化异腈和邻苯甲酰羟胺的反应

Scheme 63. Copper-catalyzed reaction of o-isocyanides and o-benzoylhydroxylamides

图式64. 铜催化邻异氰基苯甲酸酯和胺的反应

Scheme 64. Copper-catalyzed reaction of o-isocyanobenzoates and amines

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