Synthesis of 2-anilinotropones via palladium-catalyzed amination of 2-triflatotropone

Organic Letters

Volumn 2, Issue 2, 2000, Pages 219-221

  Hicks, Frederick A ^a   Brookhart, Maurice ^a  

^a The University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001236804     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991310t     Document Type: Article

References (23)

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14. (d) Suri, S. C.; Nair, V. Synthesis 1990, 695.
15. Stille coupling: (e) Banwell, M. G.; Collis, M. P.; Crisp, G. T.; Lambert, J. N.; Reum, M. E.; Scoble, J. A. J. Chem. Soc., Chem. Commun. 1989, 616.
16. (f) Banwell, M. G.; Cameron, J. M.; Collis, M. P.; Crisp, G. T.; Gable, R. W.; Hamel, E.; Lambert, J. N.; Mackay, M. F.; Reum, M. E.; Scoble, J. A. Aust. J. Chem. 1991, 44, 705.
17. Carbonylative coupling: (g) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 1557.
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20. 2 to promote phenolic substitution with 3-bromotropolone (yield increased from 49% uncatalyzed to 90%) has been reported. Takuse, K. Bull. Chem. Soc. Jpn. 1964, 37, 1288.
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22. Control reactions were conducted involving the cross coupling conditions in the absence of palladium. For 2-tosyloxytropone, only the rearranged product 3 was observed. For 2-triflatotropone, only unreacted aniline could be isolated at the end of the reaction.
23. 3): δ 8.40 (bs, 1 H); 7.32 (m, 2 H); 7.18 (m, 3 H); 7.08 (t, J = 10.5 Hz, 1 H); 6.73 (m, 1 H); 6.22 (d, J = 10.5 Hz, 1 H); 2.15 (s, 6 H).