Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions

被引：85

作者：

Li, Minyan ^{[1
]}

Yucel, Baris ^{[1
,3
]}

Adrio, Javier ^{[1
,2
]}

Bellomo, Ana ^{[1
]}

Walsh, Patrick J. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, 231 S 34th St, Philadelphia, PA 19104 USA

[2] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain

[3] Istanbul Tech Univ, Dept Chem, TR-34469 Istanbul, Turkey

来源：

CHEMICAL SCIENCE | 2014年 / 5卷 / 06期

基金：

美国国家科学基金会;

关键词：

SP(3) C-H; ALLYL DIPHENYLGLYCINATE IMINES; ASYMMETRIC-SYNTHESIS; BOND ARYLATION; DECARBOXYLATIVE ALLYLATION; ORGANOMETALLIC REAGENTS; COUPLING REACTIONS; AMINES; MILD; HYDROGENATION;

D O I：

10.1039/c3sc53526f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diarylmethylamines are of great interest due to their prevalence in pharmaceutical chemistry. As a result, new methods for their synthesis are in demand. Herein, we report a versatile protocol for the synthesis of diarylmethylamine derivatives involving palladium-catalyzed arylation of in situ generated 2-azaallyl anion intermediates. The 2-azaallyl anions are generated by reversible deprotonation of readily available aldimine and ketimine precursors. Importantly, the arylated aldimine and ketimine products do not undergo isomerization under the reaction conditions. Scale-up of the arylation and hydrolysis of the resulting products to furnish diarylmethylamines were also successfully performed.

引用

页码：2383 / 2391

页数：9

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