N-Alkylation of amines with alcohols catalyzed by a Cp*Ir complex

Tetrahedron Letters

Volumn 44, Issue 13, 2003, Pages 2687-2690

  Fujita, Ken Ichi ^a   Li, Zhenzi ^a   Ozeki, Naohiro ^a   Yamaguchi, Ryohei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Alcohol; Amine; Hydrogen transfer; Iridium catalyst; N alkylation

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; ANILINE; ANILINE DERIVATIVE; BENZYL ALCOHOL; BENZYLANILINE; CARBONIC ACID; CHLORIDE; CYCLOPENTADIENE DERIVATIVE; IRIDIUM COMPLEX; PENTAMETHYLCYCLOPENTADIENYL; POTASSIUM; TOLUENE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE;

EID: 0037463731     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00371-X     Document Type: Article

References (18)

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12. Several groups have reported hydrogen transfer reactions catalyzed by Cp*Ir complexes: (a) Mashima, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1199; (b) Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186; (c) Ogo, S.; Makihara, N.; Watanabe, Y. Organometallics 1999, 18, 5470; (d) Ogo, S.; Makihara, N.; Kaneko, Y.; Watanabe, Y. Organometallics 2001, 20, 4903; (e) Suzuki, T.; Morita, K.; Tsuchida, M.; Hiroi, K. Org. Lett. 2002, 4, 2361.
13. Several groups have reported hydrogen transfer reactions catalyzed by Cp*Ir complexes: (a) Mashima, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1199; (b) Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186; (c) Ogo, S.; Makihara, N.; Watanabe, Y. Organometallics 1999, 18, 5470; (d) Ogo, S.; Makihara, N.; Kaneko, Y.; Watanabe, Y. Organometallics 2001, 20, 4903; (e) Suzuki, T.; Morita, K.; Tsuchida, M.; Hiroi, K. Org. Lett. 2002, 4, 2361.
14. Several groups have reported hydrogen transfer reactions catalyzed by Cp*Ir complexes: (a) Mashima, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1199; (b) Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186; (c) Ogo, S.; Makihara, N.; Watanabe, Y. Organometallics 1999, 18, 5470; (d) Ogo, S.; Makihara, N.; Kaneko, Y.; Watanabe, Y. Organometallics 2001, 20, 4903; (e) Suzuki, T.; Morita, K.; Tsuchida, M.; Hiroi, K. Org. Lett. 2002, 4, 2361.
15. Several groups have reported hydrogen transfer reactions catalyzed by Cp*Ir complexes: (a) Mashima, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1199; (b) Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186; (c) Ogo, S.; Makihara, N.; Watanabe, Y. Organometallics 1999, 18, 5470; (d) Ogo, S.; Makihara, N.; Kaneko, Y.; Watanabe, Y. Organometallics 2001, 20, 4903; (e) Suzuki, T.; Morita, K.; Tsuchida, M.; Hiroi, K. Org. Lett. 2002, 4, 2361.
16. Several groups have reported hydrogen transfer reactions catalyzed by Cp*Ir complexes: (a) Mashima, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1199; (b) Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186; (c) Ogo, S.; Makihara, N.; Watanabe, Y. Organometallics 1999, 18, 5470; (d) Ogo, S.; Makihara, N.; Kaneko, Y.; Watanabe, Y. Organometallics 2001, 20, 4903; (e) Suzuki, T.; Morita, K.; Tsuchida, M.; Hiroi, K. Org. Lett. 2002, 4, 2361.
17. 3 (0.050 mmol) in toluene (0.5 mL). Then amine (1.0 mmol) and alcohol (1.0 mmol) were added, and the mixture was stirred at 110°C for 17 h in the sealed reactor. The products were isolated by silica gel column chromatography. The products were identified by NMR analysis.
18. N-Methylation by methanol was unsuccessful. N-Methylation by methanol is known to be considerably difficult. Huh K.-T., Tsuji Y., Kobayashi M., Okuda F., Watanabe Y. Chem. Lett. 1988;449.