High-yielding synthesis of Weinreb amides via homogeneous catalytic carbonylation of iodoalkenes and iodoarenes

Tetrahedron

Volumn 66, Issue 25, 2010, Pages 4479-4483

  Takács, Attila ^a   Petz, Andrea ^a   Kollár, László ^a  

^a UNIVERSITY OF PÉCS   (Hungary)

Author keywords

Aminocarbonylation; Carbon monoxide; Iodoalkene; Palladium; Weinreb amide

Indexed keywords

ALKENE DERIVATIVE; AMIDE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AMINOCARBONYLATION; ARTICLE; CARBONYLATION; CATALYSIS; PRESSURE; PRIORITY JOURNAL; SYNTHESIS;

EID: 77953119518     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.076     Document Type: Article

References (28)

1. Khlestkin V.K., and Mazhukin D.G. Curr. Org. Chem. 7 (2003) 967-993 and references cited therein
2. Sha C.-K., Huang S.-J., and Zhan Z.-P. J. Org. Chem. 67 (2002) 831-836
3. Balasubramaniam S., and Aidhen I.S. Synthesis (2008) 3707-3738 and references cited therein
4. Skoda-Földes R., and Kollár L. Curr. Org. Chem. 6 (2002) 1097-1119
5. In: Cornils B., and Herrmann W.A. (Eds). Applied Homogeneous Catalysis with Organometallic Compounds (1996), Wiley-VCH, Weinheim
6. In: Beller M., and Bolm C. (Eds). Transition Metals for Organic Synthesis Vol. I-II (1998), Wiley-VCH, Weinheim
7. Colquhoun H.M., Thompson D.J., and Twigg M.V. Carbonylation. Direct Synthesis of Carbonyl Compounds (1991), Plenum, New York, NY and London
8. Arcadi A. Carbonylation of Enolizable Ketones (Enol Triflates) and Iodoalkenes. In: Kollár L. (Ed). Modern Carbonylation Methods (2008), Wiley-VCH, Weinheim 223-250 Chapter 9
9. Horváth L., Berente Z., and Kollár L. Lett. Org. Chem. 4 (2007) 236-238
10. Balogh J., Mahó S., Háda V., Kollár L., and Skoda-Földes R. Synthesis (2008) 3040-3042
11. Ács P., Takács A., Szilágyi A., Wölfling J., Schneider G., and Kollár L. Steroids 74 (2009) 419-423 and references cited therein
12. Nahm S., and Weinreb S.M. Tetrahedron Lett. 22 (1981) 3815-3818
13. Sibi M.P. Org. Prep. Proced. Int. 25 (1993) 15-42
14. Colobert F.C., des Mazery R., Solladier G., and Carreňo M.C. Org. Lett. 4 (2002) 1723-1725
15. Williams J.M., Jobson R.B., Yasuda N., Marchesini G., Dolling U.-H., and Grabowski E.J.J. Tetrahedron Lett. 36 (1995) 5461-5464
16. Woo J.C.S., Fenster E., and Dake G.R. J. Org. Chem. 69 (2004) 8984-8986 and references cited therein
17. Murakami M., Hoshino Y., Yto H., and Yto Y. Chem. Lett. (1998) 163-164
18. Martinelli J.R., Freckmann D.M.M., and Buchwald S.L. Org. Lett. 8 (2006) 4843-4846
19. Deagostino A., Larini P., Occhiato E.G., Pizzuto L., Prandi C., and Venturello P. J. Org. Chem. 73 (2008) 1941-1945
20. Amatore C., Carre E., Jutand A., M'Barki M.A., and Meyer G. Organometallics 14 (1995) 5605-5614 and references cited therein
21. Csákai Z., Skoda-Földes R., and Kollár L. Inorg. Chim. Acta 286 (1999) 93-97
22. Takács A., Jakab B., Petz A., and Kollár L. Tetrahedron 63 (2007) 10372-10378
23. Takács A., Farkas R., Petz A., and Kollár L. Tetrahedron 65 (2009) 4795-4800
24. Müller E., Péczely G., Skoda-Földes R., Takács E., Kokotos G., Bellis E., and Kollár L. Tetrahedron 61 (2005) 797-802 and references cited therein
25. Dineen T.A., Zajac M.A., and Myers A.G. J. Am. Chem. Soc. 126 (2006) 16406-16409
26. Tunoori A.R., White J.M., and Georg G.I. Org. Lett. 2 (2000) 4091-4093
27. White J.M., Tunoori A.R., Turunen B.J., and Georg G.I. J. Org. Chem. 69 (2004) 2573-2576
28. Somich C., Mazzocchi P.H., and Ammon H.L. J. Org. Chem. 52 (1987) 3614-3619