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Iron‐Catalyzed Alkylation of Nitriles with Alcohols
Author(s) -
Ma Wei,
Cui Suya,
Sun Huamin,
Tang Weijun,
Xue Dong,
Li Chaoqun,
Fan Juan,
Xiao Jianliang,
Wang Chao
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803762
Subject(s) - alkylation , olefin fiber , nitrile , catalysis , chemistry , primary (astronomy) , organic chemistry , hydride , hydrogen , combinatorial chemistry , physics , astronomy
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.