Gold(III)-Catalyzed Synthesis of N,N-Aryl,Benzyl-amines in Water

Gold(III)/Sodium Diphenylphosphinobenzene-3-sulfonate (TPPMS) Catalyzed Dehydrative N-Benzylation of Electron-Deficient Anilines in Water: H. Hikawa, M. Matsumoto, S. Tawara, S. Kikkawa, I. Azumaya
Synthesis 2019, DOI: 10.1055/s-0037-1611519

The efficient synthesis of diversely functionalized N-substituted anilines remains an important target in organic chemistry, especially the development of catalytic and biocompatible processes. Gold(III) catalysis is emerging as a powerful strategy to access a variety of organic molecules, and recently the group lead by Associate Professor Hidemasa Hikawa and Professor Isao Azumaya at Toho University (Chiba, Japan) has disclosed a protocol – featuring broad scope and user-friendly conditions – for using gold(III) catalysis in water to generate a wide range of the target secondary amines, starting from easily accessible anilines and benzylic alcohols. 

Professor Azumaya and Associate Professor Hikawa said: “This simple protocol can be performed under mild conditions in an atom-economic process without the need for base or other additives, furnishing the electron-deficient N-benzylic anilines in moderate to excellent yields along with water as a sole co-product.” 

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