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Iron-Catalyzed Alkylation of Nitriles with Alcohols
Wei Ma1, Suiya Cui1, Huamin Sun1
1Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, Department of Chemistry and Chemical, Engineering, Shaanxi Normal University, Xi'an, 710119, P. R. China.
Abstract:
A general, efficient iron-catalyzed α-alkylation of nitriles with primary alcohols through a hydrogen-borrowing pathway has been developed, allowing a wide variety of alkylated nitriles to be readily accessible. Detailed mechanistic studies suggest that the reaction proceeds via an olefin intermediate with the turnover rate limited by the hydrogenation of the olefin with an iron hydride. Apart from participating in the alkylation, the nitrile is found to play an important role in promoting the formation of and stabilizing the active catalytic species.
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