Palladium-catalyzed oxidative alkynylation of alkenes via C-C bond cleavage under oxygen atmosphere

Organic Letters

Volumn 5, Issue 17, 2003, Pages 2997-2999

  Nishimura, Takahiro ^a   Araki, Hitoshi ^a   Maeda, Yasunari ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; CARBON; OXYGEN; PALLADIUM; REAGENT;

ALKYNYLATION; ARTICLE; ATMOSPHERE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION;

EID: 0141856128     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0348405     Document Type: Article

References (33)

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2. For reviews of C-C bond cleavage reactions, see: (a) Bishop, K. C., III. Chem. Rev. 1976, 76, 461. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (d) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (e) Murakami, M.; Ito, Y. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: New York, 1999; pp 97-129.
3. For reviews of C-C bond cleavage reactions, see: (a) Bishop, K. C., III. Chem. Rev. 1976, 76, 461. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (d) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (e) Murakami, M.; Ito, Y. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: New York, 1999; pp 97-129.
4. For reviews of C-C bond cleavage reactions, see: (a) Bishop, K. C., III. Chem. Rev. 1976, 76, 461. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (d) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (e) Murakami, M.; Ito, Y. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: New York, 1999; pp 97-129.
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21. Isolated yield; 3-phenylcyclobutanone (59%), benzophenone (59%).
22. 3 bond of substituents on the ring; see refs 5 and 6.
23. The formation of 1,3-diphenyl-2-propyn-1-one was detected by GC/MS. The isolation of it was not carried out because of its instability under these reaction conditions.
24. The fast β-carbon elimination of an alkynyl group is probably due to the strong precoordination of the π-bond of an alkyne with palladium.
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31. Al(III)- and Zr(IV)-mediated Meerwein-Ponndorf-Verley alkynylation of aldehydes using a tert-propargylic alcohol has been reported, in which the reaction proceeds via a direct migration of the alkynyl moiety to a carbonyl carbon atom. (a) Ooi, T.; Miura, T.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 10790. (b) Ooi, T.; Takaya, K.; Miura, T.; Maruoka, K. Synlett 2000, 69. (c) Ooi, T.; Miura, T.; Takaya, K.; Ichikawa, H.; Maruoka, K. Tetrahedron 2001, 57, 867.
32. Al(III)- and Zr(IV)-mediated Meerwein-Ponndorf-Verley alkynylation of aldehydes using a tert-propargylic alcohol has been reported, in which the reaction proceeds via a direct migration of the alkynyl moiety to a carbonyl carbon atom. (a) Ooi, T.; Miura, T.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 10790. (b) Ooi, T.; Takaya, K.; Miura, T.; Maruoka, K. Synlett 2000, 69. (c) Ooi, T.; Miura, T.; Takaya, K.; Ichikawa, H.; Maruoka, K. Tetrahedron 2001, 57, 867.
33. Al(III)- and Zr(IV)-mediated Meerwein-Ponndorf-Verley alkynylation of aldehydes using a tert-propargylic alcohol has been reported, in which the reaction proceeds via a direct migration of the alkynyl moiety to a carbonyl carbon atom. (a) Ooi, T.; Miura, T.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 10790. (b) Ooi, T.; Takaya, K.; Miura, T.; Maruoka, K. Synlett 2000, 69. (c) Ooi, T.; Miura, T.; Takaya, K.; Ichikawa, H.; Maruoka, K. Tetrahedron 2001, 57, 867.