Hydrogenative coupling of nitriles with diamines to benzimidazoles using lignin-derived Rh2P catalyst

iScience

Ruxu Yao¹  Tao Li¹  Yisheng Xu²  Jinzhu Chen³  Jiarui Zhang³ 

[1] College of Chemistry and Materials Science, Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, Jinan University, Guangzhou 511443, China;College of Chemistry and Materials Science, Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, Jinan University, Guangzhou 511443, China;State Key Laboratory of Chemical Engineering, International Joint Research Center of Green Energy Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China;

关键词: chemistry;    inorganic chemistry;    catalysis;    organic chemistry;    organic synthesis;   

DOI  :  

来源: DOAJ

【 摘 要 】

Summary: Nitrile (C≡N bond) activation for direct organic synthesis has been less explored so far due to a high redox potential of nitrile and its low dissociation energy of C−CN bond. Herein, we demonstrate a direct reductive coupling of nitriles and 1,2-phenylenediamines to yield various benzimidazoles in excellent yields (95%–99%) by using rhodium phosphide (Rh2P) catalyst supported on lignin-derived carbon (LC) using H2 (or hydrazine hydrate) as a hydrogen source. The high catalytic performance of Rh2P/LC is attributed to enhanced charge transfer to Rh and strong P−Rh interactions. Our isotope trace experiment confirms the presence of H/D exchange between H2 and the inert –CD3 group of CD3CN via an intramolecular D-shift. Reusability of Rh2P/LC is further demonstrated by a seven-time recycling without evident loss of activity. This research thus highlights a great potential in organic transformation with nitrile as a synthetic building block.

【 授权许可】

Unknown