Ru-catalyzed hydroamidation of alkenes and cooperative aminocarboxylation procedure with chelating formamide

Organic Letters

Volumn 5, Issue 15, 2003, Pages 2687-2690

  Ko, Sangwon ^a   Han, Hoon ^a   Chang, Sukbok ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINE; CARBON MONOXIDE; FORMAMIDE; IODINE DERIVATIVE; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RUTHENIUM COMPLEX;

AMIDATION; ARTICLE; CARBOXYLATION; CATALYSIS; CATALYST; CHELATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; HYDROGEN BOND; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0141520397     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034862r     Document Type: Article

References (47)

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35. For experimental details, see Supporting Information.
36. Regioselectivity of exo/endo isomer was determined unambiguously by comparison to the literature after hydrolysis of the obtained amide to the corresponding carboxylic acid; see: Eda, M.; Takemoto, T.; Ono, S.-i.; Okada, T.; Kosaka, K.; Gohda, M.; Matzno, S.; Nakamura, N.; Fukaya, C. J. Med. Chem. 1994, 37, 1983.
37. We isolated a triruthenium cluster bound to 2-pyridylmethanol from the previous studies and showed that it was a stoichiometric reagent for the hydroesterification of alkenes. For a reference, see ref 6b.
38. For some recent examples of sequential catalytic reactions, see: (a) Jeong, N.; Seo, S. D.; Shin, J. Y. J. Am. Chem. Soc. 2000, 122, 10220. (b) Park, K. H.; Son, S. U.; Chung, Y. K. Org. Lett. 2002, 4, 4361.
39. For some recent examples of sequential catalytic reactions, see: (a) Jeong, N.; Seo, S. D.; Shin, J. Y. J. Am. Chem. Soc. 2000, 122, 10220. (b) Park, K. H.; Son, S. U.; Chung, Y. K. Org. Lett. 2002, 4, 4361.
40. On the basis of this result, the possibility that DMF acts as a CO source through decomposition of the solvent can be ruled out. For a reference of a related example, see: Wan, Y.; Altermann, M.; Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67, 6232.
41. Recent example of aminocarbonylation of aryl iodides using DMF as an amide source: Hosoi, K.; Nozaki, K.; Hiyama, T. Org. Lett. 2002, 4, 2849.
42. Use of aldehyde as a CO source in catalytic Pauson-Khand reaction has been reported recently; see: (a) Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Am. Chem. Soc. 2002, 124, 3806. (b) Shibata, T.; Toshida, N.; Takagi, K. Org. Lett. 2002, 4, 1619.
43. Use of aldehyde as a CO source in catalytic Pauson-Khand reaction has been reported recently; see: (a) Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Am. Chem. Soc. 2002, 124, 3806. (b) Shibata, T.; Toshida, N.; Takagi, K. Org. Lett. 2002, 4, 1619.
44. For recent reviews of hydroamination, see: (a) Gasc, M. B.; Lattes, A.; Perie, J. J. Tetrahedron 1983, 39, 703. (b) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675. (c) Nobis, M.; Driessen-Holscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983. (d) Müller, T. E.; Beller, M. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 2, p 316.
45. For recent reviews of hydroamination, see: (a) Gasc, M. B.; Lattes, A.; Perie, J. J. Tetrahedron 1983, 39, 703. (b) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675. (c) Nobis, M.; Driessen-Holscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983. (d) Müller, T. E.; Beller, M. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 2, p 316.
46. For recent reviews of hydroamination, see: (a) Gasc, M. B.; Lattes, A.; Perie, J. J. Tetrahedron 1983, 39, 703. (b) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675. (c) Nobis, M.; Driessen-Holscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983. (d) Müller, T. E.; Beller, M. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 2, p 316.
47. For recent reviews of hydroamination, see: (a) Gasc, M. B.; Lattes, A.; Perie, J. J. Tetrahedron 1983, 39, 703. (b) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675. (c) Nobis, M.; Driessen-Holscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983. (d) Müller, T. E.; Beller, M. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 2, p 316.