Palladium‐Catalyzed N‐Alkylation of Amides and Amines with Alcohols Employing the Aerobic Relay Race Methodology |
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Authors: | Xiaochun Yu Lan Jiang Qiang Li Yuanyuan Xie Qing Xu |
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Institution: | 1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035, China;2. College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, China |
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Abstract: | 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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Keywords: | palladium catalysis amides amines alcohols N‐alkylation reaction aerobic reaction relay race methodology |
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