Ruthenium-catalyzed intermolecular coupling reactions of arylamines with ethylene and 1,3-dienes: mechanistic insight on hydroamination vs ortho-C-H bond activation. Org Lett 2005 May 26;7(11):2181-3
Date
05/20/2005Pubmed ID
15901164DOI
10.1021/ol050524+Scopus ID
2-s2.0-20444470280 (requires institutional sign-in at Scopus site) 76 CitationsAbstract
[reaction: see text]. The cationic ruthenium complex [(PCy3)2(CO)(Cl)Ru=CHCH=C(CH3)2]+BF4- was found to be an effective catalyst for the coupling reaction of aniline and ethylene to form a approximately 1:1 ratio of N-ethylaniline and 2-methylquinoline products. The analogous reaction with 1,3-dienes resulted in the preferential formation of Markovnikov addition products. The normal isotope effect of k(NH)/k(ND) = 2.2 (aniline and aniline-d7 at 80 degrees C) and the Hammett rho = -0.43 (correlation of para-substituted p-X-C6H4NH2) suggest an N-H bond activation rate-limiting step for the catalytic reaction.
Author List
Yi CS, Yun SYAuthor
Chae Yi PhD Professor, Inorganic and Organometallic Chemistry, Homogeneous Catalysis in the Chemistry department at Marquette UniversityMESH terms used to index this publication - Major topics in bold
AlkadienesAmines
Aniline Compounds
Catalysis
Ethylenes
Isotopes
Quinolines
Ruthenium
