Silver-Catalyzed, N-Formylation of Amines Using Glycol Ethers

被引：10

作者：

King, Bradley H. ^{[1
]}

Wang, Michelle L. ^{[1
]}

Jesse, Kate A. ^{[1
]}

Kaur, Guneet ^{[1
]}

Tran, Brianna ^{[1
]}

Walser-Kuntz, Ryan ^{[2
]}

Iafe, Robert G. ^{[3
]}

Wenzel, Anna G. ^{[1
]}

机构：

[1] Claremont McKenna & Pitzer Coll, Keck Sci Dept, Scripps, Claremont, CA 91711 USA

[2] Univ Michigan, Ann Arbor, MI 48109 USA

[3] Calif State Univ, Dept Chem & Biochem, San Marcos, CA 92078 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 20期

基金：

美国国家科学基金会;

关键词：

CONVENIENT PROCEDURE; HYDROGEN-PEROXIDE; COINAGE METALS; GOLD CATALYSIS; ACID ESTERS; CATION; CONVERSION; MECHANISM; OXIDATION; METHANOL;

D O I：

10.1021/acs.joc.0c01552

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A silver-catalyzed protocol was found to afford the N-formylation of amines in moderate-to-good yields. Ethylene glycol-derived, oligomeric ethers were found to function as the formylating agent, with 1,4-dioxane affording the best results. This reaction does not require the use of stoichiometric activating reagents, and avoids the use of explosive reagents or toxic gases, such as CO, as the Cl synthon. Mechanistic studies indicate a single-electron transfer-based pathway. This work highlights the ability of silver to participate in unexpected reaction pathways.

引用

页码：13256 / 13263

页数：8

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