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Palladium‐Catalyzed N‐ Alkylation of Amides and Amines with Alcohols Employing the Aerobic Relay Race Methodology
Author(s) -
Yu Xiaochun,
Jiang Lan,
Li Qiang,
Xie Yuanyuan,
Xu Qing
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201200462
Subject(s) - chemistry , catalysis , alkylation , palladium , alcohol , homogeneous catalysis , homogeneous , alcohol oxidation , ligand (biochemistry) , allyl alcohol , combinatorial chemistry , organic chemistry , receptor , biochemistry , physics , thermodynamics
Possibly because homogeneous palladium catalysts are not typical borrowing hydrogen catalysts and ligands are thus ineffective in catalyst activation under conventional anaerobic conditions, they had not been used in the N‐ alkylation reactions of amines/amides with alcohols in the past. By employing the aerobic relay race methodology with Pd‐catalyzed aerobic alcohol oxidation being a more effective protocol for alcohol activation, ligand‐free homogeneous palladiums are successfully used as active catalysts in the dehydrative N‐ alkylation reactions, giving high yields and selectivities of the alkylated amides and amines. Mechanistic studies implied that the reaction most probably proceeds via the novel relay race mechanism we recently discovered and proposed.