Nickel-catalyzed addition of P(O)-H bonds to propargyl alcohols: One-pot generation of phosphinoyl 1,3-butadienes

Organic Letters

Volumn 7, Issue 14, 2005, Pages 2909-2911

  Han, Li Biao ^a   Ono, Yutaka ^a   Yazawa, Hideaki ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

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Indexed keywords

EID: 22244474298     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0508431     Document Type: Article

References (28)

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17. (a) Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080.
18. For related examples: (b) Sadow, A. D.; Haller, I.; Fadini, L.; Togni, A. J. Am. Chem. Soc. 2004, 126, 14704.
19. (b) Ribière, P.; Bravo-Altamirano, K.; Antczak, M. I.; Hawkins, J. D.; Montchamp, J.-L. J. Org. Chem. 2005, 70, 4064.
20. 2P(O)OH was used as the catalyst, (a) Han, L.-B.; Zhao, C.-Q.; Onozawa, S.-y.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842.
21. (b) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc. 2000, 122, 5407.
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24. 2PH to propargyl alcohols: Jérôme, F.; Monnier, F.; Lawicka, H.; Dérien, S.; Dixneuf, P. H. Chem. Commun. 2003, 696.
25. (f) Ru-catalyzed double phosphinylation of propargyl alcohols: Milton, M. D.; Onodera, G.; Nishibayashi, Y.; Uemura, S. Org. Lett. 2004, 6, 3993.
26. Surprisingly, a similar in situ dehydration did not take place with a secondary propargyl alcohol 3-butyn-2-ol.
27. 3 completely retarded the formation of the corresponding dehydration products.
28. 2P(O)H to give the adducts.