Recent Advances in Transition Metal-Catalyzed Isocyanide Insertion Reactions

doi:10.6023/cjoc202204007

Abstract

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

Cite this article

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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Fig. & Tab. 64

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

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

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

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

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

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

Scheme 7. Synthesis of quinoline derivatives under palladium catalytic system

Scheme 8. Synthesis of isoindolones under palladium-catalyzed system

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 22. Palladium-catalyzed reaction of tetraarylleads and isocyanides

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

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

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

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

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

Scheme 28. Palladium-catalyzed reaction of enamides and isocyanides

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

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

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

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

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

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

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

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

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

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

Scheme 39. Palladium-catalyzed reaction of amidoximes and isocyanides

Scheme 40. Palladium-catalyzed reaction of isoxazolones and isocyanides

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

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

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

Scheme 44. Synthesis of enoneimines under palladium-catalyzed system

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

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

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

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

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

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

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

Scheme 52. Cobalt-catalyzed reaction of arylamides and isocyanides

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

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

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

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

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

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

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

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

Scheme 61. Rhodium-catalyzed coupling reaction involving isocyanides

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

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

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

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