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

被引：84
|
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
收藏
页码：2383 / 2391
页数：9
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