Nickel-catalyzed reactions of vinyl aziridines and aziridinylen-ynes

Tetrahedron Letters

Volumn 49, Issue 48, 2008, Pages 6797-6799

  Zuo, Gang ^a   Zhang, Kainan ^a   Louie, Janis ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Aziridinylen ynes; Heterocycles; Imines; N Heterocyclic carbene; Nickel catalyst; Vinyl aziridine

Indexed keywords

ALKYNE DERIVATIVE; AZIRIDINE DERIVATIVE; NICKEL;

ARTICLE; CATALYSIS; CHEMICAL REACTION;

EID: 53549127548     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.056     Document Type: Article

References (53)

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13. Thermal or nucleophile-promoted rearrangements of vinylaziridines generally lead to two different tautomers of pyrroline. Atkinson R.S., and Rees C.W. Chem. Commun. (1967) 1232
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21. 3, ppm): δ 144.6, 139.4, 129.8, 127.6, 126.8, 116.5, 74.5, 35.0, 29.2.
22. IPr = 1,3-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene; SIPr = 1,3-bis(2,5-diisopropylphenyl)-4,5-dihydroimidazolin-2-ylidene; IMes = 1,3-bis(2,4,6-trimethylphenyl)-imidazol-2-ylidene; ItBu = 1,3-di-tert-butylimidazol-2-ylidene.
23. 3, ppm): δ 7.61 (d, 1H), 7.49 (d, 6H), 7.09-7.20 (m, 9H), 6.60 (dd, 1H), 5.53 (dq, 1H), 1.45 (d, 3H).
24. 1,5-H shifts of vinyl aziridines to conjugated imines have been observed:. Borel D., Gelas-Mialhe Y., and Vessière R. Can. J. Chem. 54 (1976) 1590
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34. 3, ppm): δ 7.79 (d, 1H), 7.49 (d, 4H), 7.09-7.20 (m, 6H), 6.43 (dd, 1H), 5.76 (dq, 1H), 5.32 (s, 1H), 1.45 (d, 3H).
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38. 6, ppm): δ 161.8, 135.9, 117.8, 80.4, 39.2, 32.6, 27.9.
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45. A similar reaction has been observed in the Ni-catalyzed rearrangement of acylvinylcyclopropanes to dihydrofurans:. Bowman R.K., and Johnson J.S. Org. Lett. 8 (2006) 573
46. 3, ppm): δ 7.15-7.83 (m, 11H), 5.68 (m, 1H), 5.26 (dd, 17.1 Hz, 1.2 Hz, 1H), 5.11 (dd, 10.2 Hz, 1.2 Hz, 1H), 3.59 (s, 1H), 2.11 (m, 1H), 1.88 (d, 3.3 Hz, 1H), 1.73 (d, 6.6 Hz, 1H).
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50. 3, ppm): δ 144.6, 135.6, 129.7, 128.0, 127.6, 126.9, 82.6, 74.5, 69.7, 58.4, 57.4, 33.9, 29.3, 3.8.
51. 6, ppm): δ 144.8, 141.3, 133.6, 130.0, 129.0, 127.2, 94.9, 80.1, 79.4, 56.0, 36.0, 17.5.
52. 3, ppm): δ 136.2, 127.2, 82.6, 75.3, 69.9, 57.7, 53.3, 32.8, 28.4, 26.7, 3.8.
53. 6, ppm): δ 144.2, 144.0, 133.5, 127.2, 127.0, 82.0, 78.4, 76.1, 69.3, 57.5, 40.7, 35.8, 3.2.