Palladium-catalyzed carbonylative cyclization of 2-bromobenzaldehyde with primary amines leading to isoindolin-1-ones

Tetrahedron Letters

Volumn 50, Issue 18, 2009, Pages 2097-2099

  Cho, Chan Sik ^a   Ren, Wen Xiu ^a  

^a Kyungpook National University   (South Korea)

Author keywords

2 Bromobenzaldehyde; Carbonylative cyclization; Isoindolin 1 ones; Palladium catalyst; Primary amines

Indexed keywords

2 BROMOBENZALDEHYDE; AMINE; BENZALDEHYDE DERIVATIVE; CARBON MONOXIDE; INDOLE DERIVATIVE; ISOINDOLIN 1 ONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; POLYMERIZATION; TEMPERATURE MEASUREMENT;

EID: 62349111557     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.109     Document Type: Article

References (34)

1. Tsuji J. Palladium Reagents and Catalysis (1995), Wiley, Chichester
2. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis (2002), Wiley, New York
3. Colquhoun H.M., Thompson D.J., and Twigg M.V. Carbonylation: Direct Synthesis of Carbonyl Compounds (1991), Plenum Press, New York p 173
4. For physiological activities of isoindolin-1-ones, see:. Takahashi I., Kawakami T., Hirano E., Yokota H., and Kitajima H. Synlett (1996) 353 and references cited therein
5. Cho C.S., Lee J.W., Lee D.Y., Shim S.C., and Kim T.J. Chem. Commun. (1996) 2115
6. Cho C.S., Chu D.Y., Lee D.Y., Shim S.C., Kim T.-J., Lim W.T., and Heo N.H. Synth. Commun. 27 (1997) 4141
7. Cho C.S., Jiang L.H., and Shim S.C. Synth. Commun. 28 (1998) 849
8. Grigg R., Zhang L., Collard S., and Keep A. Tetrahedron Lett. 44 (2003) 6979
9. Okuro K., Inokawa N., Miura M., and Nomura M. J. Chem. Res. (S) (1994) 372
10. Cho C.S., Lim D.K., Zhang J.Q., Kim T.-J., and Shim S.C. Tetrahedron Lett. 45 (2004) 5653
11. Cho C.S., Patel D.B., and Shim S.C. Tetrahedron 61 (2005) 9490
12. Cho C.S., Shim H.S., Choi H.-J., Kim T.-J., Shim S.C., and Kim M.C. Tetrahedron Lett. 41 (2000) 3891
13. Cho C.S., Lim D.K., Heo N.H., Kim T.-J., and Shim S.C. Chem. Commun. (2004) 104
14. Cho C.S. J. Organomet. Chem. 690 (2005) 4094
15. Cho C.S., and Patel D.B. Tetrahedron 62 (2006) 6388
16. Cho C.S., and Patel D.B. J. Mol. Catal. A: Chem. 260 (2006) 105
17. Cho C.S., and Kim J.U. Tetrahedron Lett. 48 (2007) 3775
18. Cho C.S., and Ren W.X. J. Organomet. Chem. 692 (2007) 4182
19. For our reports on palladium-catalyzed carbonylative cyclizations, see:. Cho C.S., and Shim H.S. Tetrahedron Lett. 47 (2006) 3835 and references cited therein
20. For 2-bromobenzaldehydes as a useful annulation counterpart, see:. Larock R.C., and Doty M.J. J. Org. Chem. 58 (1993) 4579
21. Gevorgyan V., Quan L.G., and Yamamoto Y. Tetrahedron Lett. 40 (1999) 4089
22. Dyker G., and Grundt P. Tetrahedron Lett. 37 (1996) 619
23. Terao Y., Satoh T., Miura M., and Nomura M. Tetrahedron 56 (2000) 1315
24. Pri-Bar I., and Buchman O. J. Org. Chem. 51 (1986) 734
25. Larock R.C., and Babu S. Tetrahedron Lett. 28 (1987) 5291
26. Schreiner S., Yu J.Y., and Vaska L. J. Chem. Soc., Chem. Commun. (1988) 602
27. Yu J.Y., Schreiner S., and Vaska L. Inorg. Chim. Acta 170 (1990) 145
28. Schumacher N., Boisen A., Dahl S., Gokhale A.A., Kandoi S., Grabow L.C., Dumesic J.A., Mavrikakis M., and Chorkendorff I. J. Catal. 229 (2005) 265
29. 2O seems to reduce the product yield by imine hydrolysis.
30. Cho C.S., Kim J.U., and Choi H.-J. J. Organomet. Chem. 693 (2008) 3677
31. 2.
32. 3) δ 46.48, 49.55, 122.89, 123.96, 127.79, 128.15, 128.26, 128.91, 131.49, 132.69, 137.11, 141.34, 168.62.
33. Yamamoto I., Tabo Y., and Gotoh H. Tetrahedron Lett. (1971) 2295
34. Wada Y., Nagasaki H., Tokuda M., and Orito K. J. Org. Chem. 72 (2007) 2008