Palladium/benzoic acid catalyzed hydroamination of alkynes

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4570-4571

  Kadota, Isao ^a   Shibuya, Akinori ^a   Lutete, Leopold Mpaka ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALKADIENE; ALKYNE; ALLENE DERIVATIVE; BENZOIC ACID; CYCLOPROPANE; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; SYNTHESIS;

EID: 0033603485     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990498r     Document Type: Article

References (16)

1. For recent review of catalytic hydroamination, see: Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
2. Armbruster, R. W.; Morgan, M. M.; Schmidt, J. L.; Lau, C. M.; Riley, R. M.; Zabrowski, D. L.; Dieck, H. A. Organometallics 1986, 5, 234-237.
3. (a) Besson, L.; Goré, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3857-3860.
4. (b) Al-Masum, M.; Meguro, M.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 6071-6074. For lanthanoid-catalyzed intramolecular hydroamination of allenes, see:
5. (c) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 4871-4872.
6. Radhakrishnan, U.; Al-Masum, M.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 1037-1040.
7. Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458-6459.
8. (a) Kadota, I.; Shibuya, A.; Gyoung, Y.-S.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 10262-10263.
9. (b) Trost, B. M.; Brieden, W.; Baringhaus, K. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 1335-1336. See also ref 9.
10. For lanthanoid-catalyzed intramolecular hydroamination of alkynes, see: Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295-9306 and references therein.
11. The use of acetic acid gave slightly lower yield.
12. Trost, B. M.; Rise, F. J. Am. Chem. Soc. 1987, 109, 3161-3163.
13. For palladium-catalyzed isomerization of alkynes to allenes, see: (a) Sheng, H.; Lin, S.; Huang, Y. Tetrahedron Lett. 1988, 27, 4893-4894. (b) Trost, B. M.; Schmidt, T. J. Am. Chem. Soc. 1988, 110, 2301-2303. Lu, X.; Ji, J.; Ma, D.; Shen, W. J. Org. Chem. 1991, 56, 5774-5778.
14. For palladium-catalyzed isomerization of alkynes to allenes, see: (a) Sheng, H.; Lin, S.; Huang, Y. Tetrahedron Lett. 1988, 27, 4893-4894. (b) Trost, B. M.; Schmidt, T. J. Am. Chem. Soc. 1988, 110, 2301-2303. Lu, X.; Ji, J.; Ma, D.; Shen, W. J. Org. Chem. 1991, 56, 5774-5778.
15. For palladium-catalyzed isomerization of alkynes to allenes, see: (a) Sheng, H.; Lin, S.; Huang, Y. Tetrahedron Lett. 1988, 27, 4893-4894. (b) Trost, B. M.; Schmidt, T. J. Am. Chem. Soc. 1988, 110, 2301-2303. Lu, X.; Ji, J.; Ma, D.; Shen, W. J. Org. Chem. 1991, 56, 5774-5778.
16. For the allylation of acetic acid with alkynes via a π-allylpalladium intermediate, see ref 6b and Al-Masum, M.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 3809-3810.