Synthesis of arylallenes by palladium-catalyzed retro-propargylation of homopropargyl alcohols

Journal of the American Chemical Society

Volumn 130, Issue 15, 2008, Pages 5048-5049

  Hayashi, Sayuri ^a   Hirano, Koji ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLENE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; PROPARGYLATION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 42149150961     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800986m     Document Type: Article

References (24)

1. (a) Ma, S. In Modern Allene Chemistry; Krause, N., Hashimi, A. S. K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 595-699.
2. (b) Murakami, M.; Matsuda, T. In Modern Allene Chemistry; Krause, N., Hashimi, A. S. K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 727-815.
3. (a) Krause, N.; Hoffmann-Röder, A. In Modern Allene Chemistry; Krause, N., Hashimi, A. S. K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 997-1039.
4. (b) Hoffmann-Röder, A.; Krause, N. Angew. Chem., Int. Ed. 2004, 43, 1196-1216.
5. (c) Wan, Z.; Nelson, S. G. J. Am. Chem. Soc. 2000, 122, 10470-10471.
6. (a) Ruitenberg, K.; Kleijn, H.; Meijer, J.; Oostveen, E. A.; Vermeer, P. J. Organomet. Chem. 1982, 224, 399-405.
7. (b) Russell, C. E.; Hegedus, L. S. J. Am. Chem. Soc. 1983, 105, 943-949.
8. (c) de Graaf, W.; Boersma, J.; van Koten, G.; Elsevier, C. J. J. Organomet. Chem. 1989, 378, 115-124.
9. (d) Mukai, C.; Takahashi, Y. Org. Lett. 2005, 7, 5793-5796.
10. Tsutsumi, K.; Ogoshi, S.; Nishiguchi, S.; Kurosawa, H. J. Am. Chem. Soc. 2001, 120, 1938-1939.
11. (a) Hayashi, S.; Hirano, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2006, 128, 2210-2211.
12. (b) Iwasaki, M.; Hayashi, S.; Hirano, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 4463-4469.
13. (c) Iwasaki, M.; Hayashi, S.; Hirano, K.; Yorimitsu, H.; Oshima, K. Tetrahedron 2007, 63, 5200-5203.
14. (d) Hayashi, S.; Hirano, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 12650-12651.
15. Although the exact role of DMA is not clear at this stage, its coordination to the palladium catalysts could enhance the catalytic activity. See Supporting Information for details of reaction optimization studies.
16. 2, or Ph, resulted in no formation of the desired products.
17. Reviews for palladium-catalyzed C-C bond cleavage of tertiary alcohols: (a) Muzart, J. Tetrahedron 2005, 61, 9423-9463.
18. (b) Nishimura, T.; Uemura, S. Synlett 2004, 201-216.
19. (c) Satoh, T.; Miura, M. Top. Organomet. Chem. 2005, 14, 1-20.
20. Cross-coupling reactions of organic halides with tertiary alcohols via β-carbon elimination: (d) Nakano, M.; Satoh, T.; Miura, M. J. Org. Chem. 2006, 71, 8309-8311.
21. (e) Terao, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2001, 123, 10407-10408.
22. (f) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 11010-11011.
23. (g) Larock, R. C.; Reddy, C. K. Org. Lett. 2000, 2, 3325-3327.
24. (h) Chow, H.-F.; Wan, C.-W.; Low, K.-H.; Yeung, Y.-Y. J. Org. Chem. 2001, 66, 1910-1913.