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Titolo:
Ru-3(CO)(12)-catalyzed coupling reaction of sp(3) C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes
Autore:
Chatani, N; Asaumi, T; Yorimitsu, S; Ikeda, T; Kakiuchi, F; Murai, S;
Indirizzi:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan Osaka Univ Suita Osaka Japan 5650871 pl Chem, Suita, Osaka 5650871, Japan
Titolo Testata:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
fascicolo: 44, volume: 123, anno: 2001,
pagine: 10935 - 10941
SICI:
0002-7863(20011107)123:44<10935:RCROSC>2.0.ZU;2-U
Fonte:
ISI
Lingua:
ENG
Soggetto:
TRANSITION-METAL COMPLEXES; RUTHENIUM-CATALYZED ADDITION; CARBON-HYDROGEN BONDS; AROMATIC KETONES; ORTHO-ALKYLATION; REGIOSELECTIVE ACYLATION; DIRECT CARBONYLATION; EXCHANGE-REACTION; SECONDARY-AMINES; BENZENE-RING;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
92
Recensione:
Indirizzi per estratti:
Indirizzo: Murai, S Osaka Univ, Fac Engn, Dept Appl Chem, 2-2 Yamadaoka, Suita, Osaka5650871,Japan Osaka Univ 2-2 Yamadaoka Suita Osaka Japan 5650871 5650871,Japan
Citazione:
N. Chatani et al., "Ru-3(CO)(12)-catalyzed coupling reaction of sp(3) C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes", J AM CHEM S, 123(44), 2001, pp. 10935-10941

Abstract

Catalytic reactions which involve the cleavage of an sp(3) C-H bond adjacent to a nitrogen atom in N-2-pyridynyl alkylamines are described. The use of Ru-3(CO)(12) as the catalyst results in the addition of the sp(3) C-H bond across the alkene bond to give the coupling products. A variety of alkenes, including terminal, internal, and cyclic alkenes, can be used for the coupling reaction. The presence of directing groups, such as pyridine, pyrimidine, and an oxazoline ring, on the nitrogen of the amine is critical for asuccessful reaction. This result indicates the importance of the coordination of the nitrogen atom to the ruthenium catalyst. In addition, the natureof the substituents. on the pyridine ring has a significant effect on the efficiency of the reaction. Thus, the substitution of an electron-withdrawing group on the pyridine ring as well as a substitution adjacent to the sp(2) nitrogen in the pyridine ring dramatically retards the reaction. Cyclic amines are more reactive than acyclic ones. The choice of solvent is also very important. Of the solvents examined, 2-propanol is the solvent of choice.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 30/09/20 alle ore 12:55:10