A general and efficient aldehyde decarbonylation reaction by using a palladium catalyst

Chemical Communications

Volumn 48, Issue 35, 2012, Pages 4253-4255

  Modak, Atanu ^a   Deb, Arghya ^a   Patra, Tuhin ^a   Rana, Sujoy ^a   Maity, Soham ^a   Maiti, Debabrata ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBON MONOXIDE; PALLADIUM; SCAVENGER;

ARTICLE; CATALYST; CHEMICAL REACTION;

EID: 84859373460     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc31144e     Document Type: Article

References (38)

1. J. F. Hartwig, Organotransition Metal Chemistry, from Bonding to Catalysis, University Science Books, New York, 2010
2. J. Tsuji, in Organopalladium Chemistry for Organic Synthesis, ed. E.-I. Negishi, Wiley, NY, 2002, vol. 2, ch. VI.5.1, pp. 2648–2653
3. M. A. Garralda: Dalton Trans. 2009 3635–3645
4. K. Sen, J. C. Hackett: J. Am. Chem. Soc. 2010 132:10293–10305
5. T. Patra, S. Manna, D. Maiti: Angew. Chem., Int. Ed. 2011 50:12140–12142
6. E. Taarning, R. Madsen: Chem.–Eur. J. 2008 14:5638–5644
7. M. C. Brohmer, N. Volz, S. Brase: Synlett 2009 1383–1386
8. T. Shibata, N. Toshida, K. Takagi: Org. Lett. 2002 4:1619–1621
9. T. Morimoto, K. Fuji, K. Tsutsumi, K. Kakiuchi: J. Am. Chem. Soc. 2002 124:3806–3807
10. A. Schirmer, M. A. Rude, X. Z. Li, E. Popova, S. B. del Cardayre: Science 2010 329:559–562
11. N. Li, H. Norgaard, D. M. Warui, S. J. Booker, C. Krebs, J. M. Bollinger: J. Am. Chem. Soc. 2011 133:6158–6161
12. G. Domazetis, B. Tarpey, D. Dolphin, B. R. James: J. Chem. Soc., Chem. Commun. 1980 939–940
13. T. Iwai, T. Fujihara, Y. Tsuji: Chem. Commun. 2008 6215–6217
14. M. Kreis, A. Palmelund, L. Bunch, R. Madsen: Adv. Synth. Catal. 2006 348:2148–2154
15. P. Fristrup, M. Kreis, A. Palmelund, P. O. Norrby, R. Madsen: J. Am. Chem. Soc. 2008 130:5206–5215
16. C. M. Beck, S. E. Rathmill, Y. J. Park, J. Y. Chen, R. H. Crabtree, L. M. Liable-Sands, A. L. Rheingold: Organometallics 1999 18:5311–5317
17. D. H. Doughty, L. H. Pignolet: J. Am. Chem. Soc. 1978 100:7083–7085
18. J. Tsuji, K. Ohno: Tetrahedron Lett. 1965 3969–3971
19. J. Tsuji, T. Ohno: Synthesis 1969 157–169
20. J. O. Hawthorne, M. H. Wilt: J. Org. Chem. 1960 25:2215
21. S. Matsubara, Y. Yokota, K. Oshima: Org. Lett. 2004 6:2071–2073
22. J. W. Wilt, W. W. Pawlikowski: J. Org. Chem. 1975 40:3641–3644
23. J. Tsuji, K. Ohno: J. Am. Chem. Soc 1968 90:94–98
24. J. Tsuji, K. Ohno, T. Kajimoto: Tetrahedron Lett. 1965 50:4565–4568
25. D. Ferri, C. Mondelli, F. Krumeich, A. Baiker: J. Phys. Chem. B 2006 110:22982–22986
26. Konopka, Jessica, Green Decarbonylation of Aldehydes using Palladium(II) Acetate, 2011. Pell Scholars and Senior Theses. Paper 2070. http://escholar.salve.edu/pell_theses/2070
27. J. M. Oconnor, J. Ma: J. Org. Chem. 1992 57:5075–5077
28. B. J. Morgan, C.A. Mulrooney, M. C. Kozlowski: J. Org. Chem. 2010 75:44–56
29. K. G. Liu, A. Chougnet, W. D. Woggon: Angew. Chem., Int. Ed. 2008 47:5827–5829
30. A. Padwa, H. Zhang: J. Org. Chem. 2007 72:2570–2582
31. S. Ikeda, M. Shibuya, Y. Iwabuchi: Chem. Commun. 2007 504–506
32. F. A. Khan, B. Rout: Tetrahedron Lett. 2006 47:5251–5253
33. J. P. Malerich, T. J. Maimone, G. I. Elliott, D. Trauner: J. Am. Chem. Soc. 2005 127:6276–6283
34. M. Harmata, S. Wacharasindhu: Org. Lett. 2005 7:2563–2565
35. G. S. Weatherhead, G. A. Cortez, R. R. Schrock, A. H. Hoveyda: Proc. Natl. Acad. Sci. U. S. A. 2004 101:5805–5809
36. Metal-Catalyzed Cross-Coupling Reactions, ed. A. de Meijere and F. Diederich, Wiley-VCH, Weinheim, Germany, 2nd edn, 2004
37. J. March, Advanced Organic Chemistry, John Wiley & Sons, New York, 1985
38. N. Fontan, M. Dominguez, R. Alvarez, A. R. de Lera: Eur. J. Org. Chem. 2011 6704–6712