Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 30, Issue 10, Pages 2322-2332Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201200462
Keywords
palladium catalysis; amides; amines; alcohols; N-alkylation reaction; aerobic reaction; relay race methodology
Categories
Funding
- NNSFC [20902070]
- SRF for ROCS of SEM
- NSF [Y4100579]
- QJTP of Zhejiang Province [QJD0902004]
- Opening Foundation of Zhejing Provincial Top Key Disciplines [100061200123, 100061200134]
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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.
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