A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides

被引：53

作者：

Zheng, Bing ^{[1
,2
]}

Jia, Tiezheng ^{[2
]}

Walsh, Patrick J. ^{[2
]}

机构：

[1] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China

[2] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Penn Merck Lab High Throughput Experimentat, Philadelphia, PA 19104 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 01期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

amides; aryl halides; CC bond formation; chemoselectivity; cross-coupling; palladium; CROSS-COUPLING REACTIONS; METHOXY-N-METHYLAMIDES; C-H BONDS; ENANTIOSELECTIVE SYNTHESIS; OXIDATIVE ADDITION; RATE ACCELERATION; OXINDOLES; CHEMISTRY; COMPLEXES; REAGENTS;

D O I：

10.1002/adsc.201300851

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient system for the direct catalytic intermolecular -arylation of acetamide derivatives with aryl bromides and chlorides is presented. The palladium catalyst is supported by Kwong's indole-based phosphine ligand and provides monoarylated amides in up to 95% yield. Excellent chemoselectivities (>10:1) in the mono- and diarylation with aryl bromides were achieved by careful selection of bases, solvents, and stoichiometry. Under the coupling conditions, the weakly acidic -protons of amides (pK(a) up to 35) were reversibly depotonated by lithium tert-butoxide (LiO-t-Bu), sodium tert-butoxide (NaO-t-Bu) or sodium bis(trimethylsilyl)amide [NaN(SiMe3)(2)].

引用

页码：165 / 178

页数：14

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