Umpolung Synthesis of Diarylmethylamines via Palladium- Catalyzed Arylation of N-Benzyl Aldimines

被引：35

作者：

Li, Minyan ^{[1
]}

Yucel, Baris ^{[1
,2
]}

Jimenez, Jacqueline ^{[1
,3
]}

Rotella, Madeline ^{[1
]}

Fu, Yue ^{[1
]}

Walsh, Patrick J. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, 231 South 34th St, Philadelphia, PA 19104 USA

[2] Istanbul Tech Univ, Fac Sci, Dept Chem, TR-34469 Istanbul, Turkey

[3] Benemerita Univ Autonoma Puebla, Fac Ciencias Quim, Ave San Claudio & 14 Sur, Puebla 72570, Pue, Mexico

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 12期

关键词：

2-azaallyl anion; diarylmethylamines; NIXANTPHOS; regioselectivity; umpolung; 1,1,3-TRIARYL-2-AZAALLYL ANIONS; REGIOSELECTIVE ARYLATION; CARBONYL-COMPOUNDS; AMINE DERIVATIVES; IMINES; DIARYLMETHANES;

D O I：

10.1002/adsc.201600075

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An umpolung synthesis of diarylmethylamine derivatives is presented. This reaction entails a palladium-catalyzed arylation of 1,3-diaryl-2-azaallyl anions, in situ generated from N-benzyl aldimines. A Pd(NIXANTPHOS)-based catalyst together with hindered silylamide bases enabled the coupling of aldimines with aryl bromides in good to excellent yields without product isomerization. Moreover, regioselectivity in the arylation of unsymmetrical 1,3-diaryl-2-azaallyl anions was studied. This method is suitable for a gram scale synthesis of diarylmethylamine derivatives at room temperature without use of a glove box.

引用

页码：1910 / 1915

页数：6

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