Synthesis of allenes by palladium-catalyzed SN2′ reaction of indium organometallics with propargylic esters

Synthesis

Volumn , Issue 22, 2007, Pages 3595-3598

  Riveiros, Ricardo ^a   Sestelo, José Pérez ^a   Sarandeses, Luis A ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

Allenes; Indium organometallics; Palladium catalysis; Propargylic esters; Regioselective reactions

Indexed keywords

ALKYNYLINDIUM REAGENTS; ALLENES; INDIUM ORGANOMETALLICS; PROPARGYLIC ESTERS;

ESTERS; INDIUM COMPOUNDS; ORGANOMETALLICS; REGIOSELECTIVITY;

AMINO ACIDS;

1 (3 VINYLHEPTA 1,2 DIENYL)BENZENE; 1 (BUTA 1,2 DIENYL) 2 METHOXYBENZENE; 1,3 DIPHENYLHEPTA 1,2 DIENE; 3 [2 (PHENYLETHENYLIDENE)HEPT 1 YNYL]TRIMETHYLSILABE; 3 BUTYL 1,5 DIPHENYLPENTA 1,2 DIEN 4 YNE; ACETIC ACID DERIVATIVE; ALKYNE DERIVATIVE; ALLENE DERIVATIVE; BENZOIC ACID DERIVATIVE; BUTA 1,2 DIENYLBENZENE; CARBONIC ACID; ESTER DERIVATIVE; HEXA 3,4 DIEN 1 YNYLBENZENE; HEXA 3,4 DIEN 1 YNYLTRIMETHYLSILANE; INDIUM; ORGANOMETALLIC COMPOUND; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ROOM TEMPERATURE; SYNTHESIS;

EID: 36749042086     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983849     Document Type: Article

References (31)

1. Modern Allene Chemistry; Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004.
2. Hoffmann-Röder, A.; Krause, N. Angew. Chem. Int. Ed. 2004, 43, 1196.
3. For general references, see: (a) Tsuji, J.; Mandai, T. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004, 585.
4. (b) Alexakis, A. Pure Appl. Chem. 1992, 64, 387.
5. (c) Hoffmann-Röder, A.; Krause, N. In Modern Allene Chemistry; Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004, 51.
6. (a) Pasto, D. J.; Hennion, G. F.; Shults, R. H.; Waterhouse, A.; Chou, S.-K. J. Org. Chem. 1976, 41, 3496.
7. (b) Jeffery-Luong, T.; Linstrumelle, G. Tetrahedron Lett. 1980, 21, 5019.
8. Negishi, E.; Liu, F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002, 551.
9. Pérez, I.; Pérez Sestelo, J.; Maestro, M. A.; Mouriño, A.; Sarandeses, L. A. J. Org. Chem. 1998, 63, 10074.
10. (a) Pérez, I.; Pérez Sestelo, J.; Sarandeses, L. A. Org. Lett. 1999, 1, 1267.
11. (b) Pérez, I.; Pérez Sestelo, J.; Sarandeses, L. A. J. Am. Chem. Soc. 2001, 123, 4155.
12. (c) Pena, M. A.; Pérez, I.; Pérez Sestelo, J.; Sarandeses, L. A. Chem. Commun. 2002, 2246.
13. (d) Pena, M. A.; Pérez Sestelo, J.; Sarandeses, L. A. Synthesis 2003, 780.
14. (e) Pena, M. A.; Pérez Sestelo, J.; Sarandeses, L. A. Synthesis 2005, 485.
15. (f) Pena, M. A.; Pérez Sestelo, J.; Sarandeses, L. A. J. Org. Chem. 2007, 72, 1271.
16. (a) Rodríguez, D.; Pérez Sestelo, J.; Sarandeses, L. A. J. Org. Chem. 2003, 68, 2518.
17. (b) Baker, L.; Minehan, T. J. Org. Chem. 2004, 69, 3957.
18. (c) Rodríguez, D.; Pérez Sestelo, J.; Sarandeses, L. A. J. Org. Chem. 2004, 69, 8136.
19. Riveiros, R.; Rodríguez, D.; Pérez Sestelo, J.; Sarandeses, L. A. Org. Lett. 2006, 8, 1403.
20. (a) DPEphos = bis[o-(diphenylphosphino)phenyl] ether,
21. (b) Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J. Organometallics 1995, 14, 3081.
22. (c) Huang, Z.; Qian, M.; Babinski, D. J.; Negishi, E. Organometallics 2005, 24, 475.
23. (a) Rosini, C.; Giacomelli, C.; Salvadori, P. J. Org. Chem. 1984, 49, 3394.
24. (b) Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 8414.
25. For general experimental methods, see ref. 8a.
26. Höffe, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569.
27. Matsuda, I.; Komori, K.-I.; Itoh, K. J. Am. Chem. Soc. 2002, 124, 9072.
28. Spectroscopic and analytical data for allenes 5-9 in Table 1 have been previously reported in ref. 9. Spectroscopic and analytical data for allenes 10-13 and 15-19 are reported herein.
29. Ruitenberg, K.; Kleijn, H.; Elsevier, C. J.; Meijer, J.; Vermeer, P. Tetrahedron Lett. 1981, 22, 1451.
30. Caporusso, A. M.; Zampieri, A.; Aronica, L. A.; Banti, D. J. Org. Chem. 2006, 71, 1902.
31. Jansen, A.; Krause, N. Inorg. Chim. Acta 2006, 359, 1761.