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Updated: Oct 18, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Hydrogenative coupling of nitriles with diamines to benzimidazoles using lignin-derived Rh2P catalyst
Jiarui Zhang1,2, Ruxu Yao1,2, Jinzhu Chen2
1State Key Laboratory of Chemical Engineering, International Joint Research Center of Green Energy Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China.
Abstract:
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.
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