Copper-Catalyzed Borrowing Hydrogen Reaction for α-Alkylation of Amides with Alcohols

被引：2

作者：

Xia, Qiuling ^{[1
,2
]}

Miao, Yulong ^{[2
]}

Hu, Yue ^{[2
]}

Xie, Yinjun ^{[2
]}

Luo, Junfei ^{[1
]}

机构：

[1] Ningbo Univ, Inst Mass Spectrometry, Zhejiang Engn Res Ctr Adv Mass Spectrometry & Clin, Sch Mat Sci & Chem Engn, Ningbo 315211, Peoples R China

[2] Chinese Acad Sci, Ningbo Inst Mat Technol & Engn, Key Lab Adv Fuel Cells & Electrolyzers & Technol Z, Ningbo 315201, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 13期

基金：

中国国家自然科学基金;

关键词：

UNACTIVATED AMIDES; C-ALKYLATION; KETONES; ESTERS; PHARMACOKINETICS; PAZINACLONE; ACETAMIDES; LIGAND;

D O I：

10.1021/acs.joc.4c00404

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the first example of copper-catalyzed alpha-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 alpha,beta-unsaturated amides were the intermediates of this reaction and also disclosed the role of copper in alcohol dehydrogenation and C=C bond hydrogenation.

引用

页码：9654 / 9660

页数：7

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