ortho-Selective C-H addition of N,N-dimethyl anilines to alkenes by a yttrium catalyst

The efficient and selective ortho-alkylation of N,N-dimethyl anilines via C-H addition to alkenes was achieved for the first time using a cationic half-sandwich yttrium catalyst. This protocol constitutes a straightforward and atom-economical route for the synthesis of a new family of tertiary anili...

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Published inChemical science (Cambridge) Vol. 7; no. 8; pp. 5265 - 5270
Main Authors Song, Guoyong, Luo, Gen, Oyamada, Juzo, Luo, Yi, Hou, Zhaomin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Activation analysis
Alkenes
Aniline
Catalysts
Cationic
Chemistry
Chemistry, Multidisciplinary
Derivatives
Mathematical analysis
Physical Sciences
Science & Technology
Yttrium
TERTIARY ANILINES
ORTHO-ALKYLATION
COMPLEXES
BOND ADDITION
OLEFIN POLYMERIZATION
AROMATIC IMINES
PYRIDINES
HYDROAMINATION
COPOLYMERIZATION
HYDROARYLATION
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Summary:The efficient and selective ortho-alkylation of N,N-dimethyl anilines via C-H addition to alkenes was achieved for the first time using a cationic half-sandwich yttrium catalyst. This protocol constitutes a straightforward and atom-economical route for the synthesis of a new family of tertiary aniline derivatives with branched alkyl substituents, which are otherwise difficult to obtain. DFT calculation studies suggest that the interaction between the yttrium atom and the NMe2 group plays an important role and the intramolecular C-H activation through a sigma-bond metathesis pathway is the rate-determining step, which is consistent with the experimental KIE observations.
Bibliography:ObjectType-Article-1
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ISSN:2041-6520
2041-6539
DOI:10.1039/c6sc00833j