An inexpensive and highly stable palladium(II) complex for room temperature Suzuki coupling reactions under ambient atmosphere

Tetrahedron Letters

Volumn 50, Issue 17, 2009, Pages 1965-1968

  Guo, Mengping ^a   Zhang, Qiaochu ^a  

^a YICHUN UNIVERSITY   (China)

Author keywords

Crystal structure; Dibenzyl diisopropylphosphoramidite ligand; Mild reaction condition; Palladium complex; Suzuki reaction

Indexed keywords

ARYL HALIDE DERIVATIVE; BENZENEBORONIC ACID; DIBENZYLDIISOPROPYLPHOSPHORAMIDITE; HALIDE; PALLADIUM COMPLEX; PHOSPHORAMIDOUS ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC PARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENVIRONMENTAL TEMPERATURE; MOISTURE; ROOM TEMPERATURE; SUZUKI REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 61749089268     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.058     Document Type: Article

References (28)

1. Niyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
2. Suzuki A. J. Organomet. Chem. 576 (1999) 147
3. Bellina F., Carpita A., and Rossi R. Synthesis 15 (2004) 2419
4. Xu Q., Duan W.-L., Lei Z.-Y., Zhu Z.-B., and Shi M. Tetrahedron 61 (2005) 11225
5. Zapf A., and Beller M. Chem. Commun. (2005) 431
6. Chen T., Gao T., and Shi M. Tetrahedron 62 (2006) 6289
7. Barder T.E. J. Am. Chem. Soc. 128 (2006) 898
8. Zhang T., Wang W.-F., Gu X.-X., and Shi M. Organometallics 27 (2008) 753
9. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 37 (1998) 3387
10. Nishiyama M., Yamamoto T., and Koie Y. Tetrahedron Lett. 39 (1998) 617
11. Hartwig J.F., Kawatsura M., Hauck S.I., Shaughnessy K.H., and Alcazar-Roman L.M. J. Org. Chem. 64 (1999) 5575
12. Littke A.F., Dai C., and Fu G.C. J. Am. Chem. Soc. 122 (2000) 4020
13. Littke A.F., and Fu G.C. Angew. Chem. 114 (2002) 4350
14. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 41 (2002) 4176
15. Christmann U., and Vilar R. Angew. Chem. 117 (2005) 370
16. Christmann U., and Vilar R. Angew. Chem., Int. Ed. 44 (2005) 366
17. Jose R., Garabatos-Perera, and Holger B. J. Organomet. Chem. 693 (2008) 357
18. Urgaonkar S., Nagarajan M., and Verkade J.G. Tetrahedron Lett. 43 (2002) 8921
19. Yu S.-B., Hu X.-P., Deng J., Huang J.-D., Wang D.-Y., Duan Z.-C., and Zheng Z. Tetrahedron Lett. 49 (2008) 1253
20. Guo M.-P., Jian F.-F., and He R. Tetrahedron Lett. 46 (2005) 9017
21. Guo M.-P., Jian F.-F., and He R. Tetrahedron Lett. 47 (2006) 2033
22. Guo M.-P., Jian F.-F., and He R. J. Fluorine Chem. 127 (2006) 177
23. Slawin A.M.Z., Wainwright M., and Woollins J.D. J. Chem. Soc., Dalton Trans. (2002) 513
24. Mikhel I.S., Bernardinelli G., and Alexakis A. Inorg. Chim. Acta 359 (2006) 1826
25. 2 = 0.1326. Selected bond distances (Å) and angles (°) are shown as follows: Pd(1)-P(1) 2.2515(9), Pd(1)-P(2) 2.2570(8), Pd(1)-Cl(1) 2.3374(10), Pd(1)-Cl(1) 2.3659(9), P(1)-Pd(1)-P(2) 98.90(3), P(1)-Pd(1)-Cl(2) 174.00(4), P(2)-Pd(1)-Cl(2) 87.09(4), P(1)-Pd(1)-Cl(1) 84.59(3), P(2)-Pd(1)-Cl(1) 176.49(3), Cl(2)-Pd(1)-Cl(1) 89.42(4). Atomic coordinates, bond lengths, and angles and the other important parameters have been deposited to Cambridge Crystallographic Data Center as supplementary publication, CCDC No. 702614. Copies of this information can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1233 336033 or e-mail: deposit@ccdc.cam.ac.uk).
26. 13C NMR spectroscopy and melting points with the literature data.
27. Gong J.-F., Liu G.-Y., Du C.-X., Zhu Y., and Wu Y.-J. J. Organomet. Chem. 690 (2005) 3963
28. Xu C., Gong J.-F., Yue S.-F., Zhu Y., and Wu Y.-J. Dalton Trans. (2006) 4730