康 · 学术 | Reaction of the Day No. 1273

2024-07-26

Copper-Catalyzed Borrowing Hydrogen Reaction for α-Alkylation of Amides with Alcohols Qiuling Xia, Yulong Miao, Yue Hu, Yinjun Xie,* and Junfei Luo* School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, 315211, P. R. China —J. Org. Chem., 2024, DOI: 10.1021/acs.joc.4c00404. Recommended by Chaoyou Liu _ PDM ABSTRACT:Authors report the first example of copper-catalyzed α-alkylation of acetamides with alcohols via a borrowing hydrogen strategy. Catalyzed by the in situ-generated copper particles, acetamides and various substituted benzyl or alkyl alcohols were transformed into functionalized amides in good yields with excellent selectivity. Compared with previous work, this process is simple using commercially available Cu(OAc)2 as a precatalyst, without an additional ligand or a metal complex, and easier. Mechanistic studies revealed that aldehyde and α,β- unsaturated amides were the intermediates of this reaction and also disclosed the role of copper in alcohol dehydrogenation and C=C bond hydrogenation. Background Substrate Scope Gram-scale Reaction Plausible Mechanism Summary and Comments In summary, authors have developed a novel copper-catalyzed selective α-alkylation of unactivated amides with alcohols via a borrowing hydrogen strategy to produce functional amides.This reaction is easy to handle, quite compatible with a wide range of substrates, environmentally friendly with water as the only byproduct, and inexpensive with the use of commercially available copper salt Cu(OAc)2 as aprecatalyst without any organic ligand or inorganic support. In addition, a plausible mechanism is proposed on the basis of a preliminary mechanistic study.

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