Synthesis, characterization, and applications of novel di-2-pyridyl imine ligands

Inorganic Chemistry Communications

Volumn 13, Issue 1, 2010, Pages 54-57

  Yorke, Jake ^a   Dent, Catlin ^a   Decken, Andreas ^b   Xia, Aibing ^a  

^a MOUNT SAINT VINCENT UNIVERSITY   (Canada)

^b UNIVERSITY OF NEW BRUNSWICK   (Canada)

Author keywords

Di 2 pyridyl imines; Palladium complexes; Phosphine ligands; The Suzuki reaction

Indexed keywords

EID: 72249091057     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2009.10.013     Document Type: Article

References (40)

1. Martin B., and Buchwald S.L. Acc. Chem. Res. 41 (2008) 1461
2. Doucet H. Eur. J. Org. Chem. 12 (2008) 2013
3. Suzuki A. Chem. Commun. 38 (2005) 4759
4. Tsuji J. Palladium Reagents and Catalysts (2004), Wiley, Chichester, UK p. 288
5. Würtz S., and Glorius F. Acc. Chem. Res. 41 (2008) 1523
6. Grasa G.A., Viciu M.S., Huang J., Zhang C., Trudell M., and Nolan S.P. Organometallics 21 (2002) 2866
7. Gstöttmayr C.W.K., Böhm V.P.W., Herdtweck E., Grosche M., and Hermann W.A. Angew. Chem., Int. Ed. 41 (2002) 1363
8. Hermann W.A., Elison M., Fischer J., Kocher C., and Artus G.R.J. Angew. Chem., Int. Ed. 34 (1995) 2371
9. Saha D., Chattopadhyay K., and Ranu B.C. Tetrahedron Lett. 50 (2009) 1003
10. Han W., Liu C., and Jin Z. Adv. Synth. Catal. 350 (2008) 501
11. Kitamura Y., Sato S., Udzu T., Tsutsui A., Maegawa T., Monguchi Y., and Sajiki H. Chem. Commun. 47 (2007) 5069
12. Liu L., Zhang Y., and Xin B. J. Org. Chem. 71 (2006) 3994
13. Tao B., and Boykin D.W. J. Org. Chem. 69 (2004) 4330
14. Grasa G.A., Hiller A.C., and Nolan S.P. Org. Lett. 3 (2001) 1077
15. Tardiff B.J., Smith J.C., Duffy S.J., Vogels C.M., and Westcott S.A. Can. J. Chem. 85 (2007) 392
16. Huang Z., Song K., Liu F., Long J., Hu H., Gao H., and Wu Q. J. Polym. Sci. Part A: Polym. Chem. 46 (2008) 1618
17. Britovsek G.J.P., Baugh S.P.D., Hoarau O., Gibson V.C., Wass D.F., White A.J.P., and Williams D.J. Inorg. Chim. Acta 345 (2003) 279
18. Gibson V.C., O'Reilly R.K., Wass D.F., White A.J.P., and Williams D.J. Dalton Trans. 14 (2003) 2824
19. Laine T.V., Piironen U., Lappalainen K., Klinga M., Aitola E., and Leskelä M. J. Organomet. Chem. 606 (2000) 112
20. Koppl A., and Alt H.G. J. Mol. Catal. A: Chem. 54 (2000) 45
21. Goswami A., Ito T., Saino N., Kase K., Matsuno C., and Okamoto S. Chem. Commun. 4 (2009) 439
22. Goswami A., Ito T., and Okamoto S. Adv. Synth. Catal. 349 (2007) 2368
23. Saino N., Amemiya F., Tanabe E., Kase K., and Okamoto S. Org. Lett. 8 (2006) 1439
24. Saino N., Kogure D., Kase K., and Okamoto S. J. Organomet. Chem. 691 (2006) 3129
25. Kanas D.A., Geier S.J., Vogels C.M., Decken A., and Westcott S.A. Inorg. Chem. 47 (2008) 8727
26. Tagata T., and Nishida M. Adv. Synth. Catal. 346 (2004) 1655
27. van Laren M.W., Duin M.A., Klerk C., Naglia M., Rogolino D., Pelagatti P., Bacchi A., Pelizzi C., and Elsevier C.J. Organometallics 21 (2002) 1546
28. Kase K., Goswami A., Ohtaki K., Tanabe E., Saino N., and Okamoto S. Org. Lett. 9 (2007) 931
29. Conrad M.L., Enman J.E., Scales S.J., Zhang H., Vogels C.M., Saleh M.T., Decken A., and Westcott S.A. Inorg. Chim. Acta 358 (2005) 63
30. Oso Y., Kanatsuki D., Saito S., Nogami T., and Ishida T. Chem. Lett. 37 (2008) 760
31. Barbaro P., Bianchini C., Giambastiani G., Rios I.G., Meli A., Oberhauser W., Segarra A.M., Sorace L., and Toti A. Organometallics 26 (2007) 4639
32. Chatani N., Tobisu M., Asaumi T., and Murai S. Synthesis 7 (2000) 925
33. -1): 2963 (s), 2923 (s), 2865 (s), 1630 (s), 1582 (s), 1568 (m), 1478 (s), 1469 (s), 1321 (s), 1138 (s), 934 (s), 854 (m), 804 (m), 748 (s), 661 (s).
34. -1): 3047 (m), 2999 (m), 2964 (s), 2958 (m), 2915 (m), 1630 (s), 151 (s), 1567 (s), 1463 (s), 1433 (s), 1360 (m), 1320 (s), 994 (s), 971 (m), 783 (s), 760 (m), 745 (s), 735 (s), 685 (m).
35. -1): 3070 (m), 2970 (m), 2914 (m), 1608 (w), 1588 (s), 1578 (s), 1474 (s), 1462 (m), 1374 (w), 1345 (m), 1143 (m), 996 (m), 855 (m), 750 (s), 633 (m), 612 (m).
36. 2 = 0.0881.
37. Laine T.V., Klinga M., and Leskelä M. Eur. J. Inorg. Chem. 6 (1999) 959
38. 2, a ligand, and a base in 5 mL of solvent under argon and heated to 100 °C for 18 h. The mixture was then cooled to room temperature, filtered, and removed off volatiles under a reduced pressure. The organic products were extracted with ether and analyzed on an Agilent 6890 GC-FID instrument. The GC yield was based on p-bromoanisole and calibrated relative to a standard containing authentic samples of p-bromoanisole and p-methoxybiphenyl.
39. Jung I.G., Son S.U., Park K.H., Chung K.-C., Lee J.W., and Chung Y.K. Organometallics 22 (2003) 4715
40. Schareina T., and Kempe R. Angew. Chem., Int. Ed. 41 (2002) 1521