Stoichiometric aryl nitrile formation from amides and aroyl isocyanates using high-valent early transition metal complexes and a catalytic process from the aroyl isocyanates

Polyhedron

Volumn 30, Issue 4, 2011, Pages 632-637

  Boyd, Peter D W ^a   Glenny, Mark G ^a   Rickard, Clifton E F ^a   Nielson, Alastair J ^b  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b MASSEY UNIVERSITY   (New Zealand)

Author keywords

Aryl nitrile; Catalysis; DFT; Mechanism; Transition metal

Indexed keywords

EID: 79951673834     PISSN: 02775387     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.poly.2010.11.032     Document Type: Article

References (37)

1. R.C. Larock Comprehensive Organic Transformations 1989 VCH New York p. 151
2. R. Wagner, and H. Zook Synthetic Organic Chemistry 1953 John Wiley and Sons New York p. 596
3. D.T. Mowry Chem. Rev. 42 1948 189
4. L.G. Humber, and M.A. Davis Can. J. Chem. 44 1966 2113
5. K. Friedrich, and H.J. Gallmeier Tetrahedron Lett. 22 1981 2971
6. S. Yamada, K. Tomoika, and K. Koga Tetrahedron Lett. 1 1976 57
7. P. Yates, and D.J. Bichan Can. J. Chem. 53 1975 2045
8. J.E. Baldwin, and C.G. Carter J. Org. Chem. 48 1983 3912
9. J.A. Krynitsky, and H.W. Carhart Organic Syntheses Coll. vol. iv 1963 Wiley New York p. 436
10. V.C. Gibson, T.P. Kee, and A. Shaw Polyhedron 9 1990 2293
11. R.R. Schrock, R.T. DePue, J. Feldman, K.B. Yap, D.C. Yang, W.M. Davis, L. Park, M. DiMare, M. Schofield, J. Anhaus, E. Walborsky, E. Evitt, C. Kruger, and P. Betz Organometallics 9 1990 2262
12. A.J. Nielson, and R.A. Anderson Inorg. Synth. 23 1985 195
13. A.J. Speziale, L.R. Smith, and J.E. Fedder J. Org. Chem. 30 1965 4306
14. A.J. Speziale, and L.R. Smith J. Org. Chem. 28 1963 1805
15. sadabs: Area-Detector Absorption Correction, Siemens Industrial Automation, Inc., Madison, WI, 1996.
16. G.M. Sheldrick Acta Crystallogr., Sect. A 64 2008 112
17. G.M. Sheldrick, shelx97 [Includes shelxs97, shelxl97, ciftab (and SHELXA?)]-Programs for Crystal Structure Analysis (Release 97-2). Institüt für Anorganische Chemie der Universität, Tammanstrasse 4, D-3400 Göttingen, Germany, 1997.
18. L.J. Furrugia J. Appl. Crystallogr. 30 1997 565
19. A.D. Becke J. Chem. Phys. 98 1993 5648
20. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B. 37 1988 785
21. P.J. Stephens, F.J. Devlin, and C.F. Chabalowski J. Phys. Chem. 98 1994 11623
22. W.R. Wadt, and P.J. Hay J. Chem. Phys. 82 1985 284
23. P.J. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 299
24. A. Ariafard, N.J. Brookes, T. Stranger, and B.F. Yates J. Am. Chem. Soc. 130 2008 11928
25. R. Krishnan, J.S. Binkley, R. Seeger, and J.A. Pople J. Chem. Phys. 72 1980 650
26. A.D. McLean, and G.S. Chandler J. Chem. Phys. 72 1980 5639
27. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, gaussian 03, (Revision A.03), Gaussian, Inc., Pittsburgh PA, 2003.
28. A.J. Nielson, P.A. Hunt, C.E.F. Rickard, and P. Schwerdtfeger J. Chem. Soc., Dalton Trans. 1997 3311
29. G.W.A. Fowles, and J.L. Frost J. Chem. Soc. A 1967 671
30. J.D. Wilkins J. Organomet. Chem. 1975 27
31. H. Funk, and G. Mohaupt Zeit. Anorg. Allge. Chem. 315 1962 204
32. M.W. Glenny, A.J. Nielson, and C.E.F. Rickard Polyhedron 17 1997 851
33. M. Kersting, A. El-Kholi, U. Muller, and K. Dehnicke Chem. Ber. 122 1989 279
34. B.R. Sreenathan, and S.L. Chadha J. Inorg. Nucl. Chem. 28 1966 1225
35. D.C. Bradley, M.B. Hursthouse, K.M.A. Malik, and A.J. Nielson J. Chem. Soc., Chem. Commun. 1981 103
36. D.C. Bradley, M.B. Hursthouse, K.M.A. Malik, A.J. Nielson, and R.L. Short J. Chem. Soc., Dalton Trans. 1983 2651
37. A.J. Nielson, R.E. McCarley, S.L. Laughlan, and C.D. Carlson Inorg. Synth. 24 1986 193