Microwave-assisted palladium-catalysed carbonylations of aryl and heteroaryl halides with sulfamide nucleophiles utilising a solid CO source

Tetrahedron Letters

Volumn 51, Issue 40, 2010, Pages 5341-5343

  Liptrot, David ^a   Alcaraz, Lilian ^a   Roberts, Bryan ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

Acyl sulfamides; Carbonylation; Homogeneous catalysis; Microwave chemistry; Palladium; Sulfamides

Indexed keywords

BROMOBENZENE; CARBON MONOXIDE; HALIDE; NUCLEOPHILE; PALLADIUM; SULFANILAMIDE;

ARTICLE; CARBONYLATION; CATALYSIS; MICROWAVE RADIATION;

EID: 77956342655     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.08.009     Document Type: Article

References (23)

1. M. Stocks, and L. Alcaraz E. Griffen, On Medicinal Chemistry 1st ed. 2007 Sci.Ink Oxford
2. C.G. Wermuth, The Practice of Medicinal Chemistry 2nd ed. 2003 Academic Press London
3. J.D. Albright, V.G. DeVries, M.T. Du, E.E. Largis, T.G. Miner, M.F. Reich, and R.G. Shepherd J. Med. Chem. 26 1983 1393
4. Raboisson, P. J. B.; Hu, L.; Vendeville, S.; Nyanguile, O. WO Filing 2009080836, 2009; Chem. Abst. 2009, 151, 124047.
5. M.P. Winters, C. Crysler, N. Subasinghe, D. Ryan, L. Leong, S. Zhao, R. Donatelli, E. Yurkow, M. Mazzulla, L. Boczon, C.L. Manthey, C. Molloy, H. Raymond, L. Murray, L. McAloman, and B. Tomczuk Bioorg. Med. Chem. Lett. 18 2008 1926
6. A.B. Reitz, G.R. Smith, and M.H. Parker Expert Opin. Ther. Patents 19 2009 1449
7. For selected examples from recent literature see: Gentles, R. G.; Ding, M.; Hewawasam, P. U.S. Patent 2007275930, 2007; Chem. Abst. 2007, 148, 11085.
8. Schmidt, T.; Gebhardt, J.; Loehr, S.; Keil, M.; Wevers, J. H.; Rack, M.; Mayer, G.; Pleschke, A. WO Filing 2007063028, 2007; Chem. Abst. 2007, 147, 52713.
9. V. Ravindranadh, H. Somu, H. Boshoff, C. Qiao, E.M. Bennett, E. Clifton, C.E. Barry III, and C.C. Aldrich J. Med. Chem. 49 2006 31
10. B. Roberts, D. Liptrot, and L. Alcaraz Org. Lett. 12 2010 1264
11. J. Georgson, A. Hallberg, and M. Larhed J. Comb. Chem. 5 2003 350
12. X. Wu, P. Nilsson, and M. Larhed J. Org. Chem. 70 2005 346
13. X. Wu, and M. Larhed Org. Lett. 7 2005 3327
14. J. Wannberg, D. Dallinger, C.O. Kappe, and M. Larhed J. Comb. Chem. 7 2005 574
15. J. Wannberg, N.F.K. Kaiser, L. Vrang, B. Samuelsson, M. Larhed, and A. Hallberg J. Comb. Chem. 7 2005 611
16. X. Wu, J.K. Ekegren, and M. Larhed Organometallics 25 2006 1434
17. X. Wu, J. Wannberg, and M. Larhed Tetrahedron 62 2006 4665
18. During the course of our work with sulfamides we have observed that they can undergo base catalysed thermal decomposition to release the corresponding amine. L. Alcaraz, C. Bennion, J. Morris, P. Meghani, and S.M. Thom Org. Lett. 6 2004 2705
19. This has also previously been reported in the literature: J. Kavalek, U. Kralikova, V. Machacek, M. Seldlak, and V. Sterba Collect. Czech. Chem. Commun. 55 1990 202
20. X. Wu, R. Rönn, T. Gossas, and M. Larhed J. Org. Chem. 70 2005 3094
21. L.R. Odell, J. Sävmarker, and M. Larhed Tetrahedron Lett. 49 2008 6115
22. O. Lagerlund, and M. Larhed J. Comb. Chem. 8 2006 4
23. J.-Y. Winum, L. Toupet, V. Barragan, G. Dewynter, and J.L. Montero Org. Lett. 3 2001 2241