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Nickel/Cobalt‐Catalyzed Reductive Hydrocyanation of Alkynes with Formamide as the Cyano Source, Dehydrant, Reductant, and Solvent
Author(s) -
Zhang Jin,
Luo CuiPing,
Yang Luo
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000935
Subject(s) - hydrocyanation , chemistry , formamide , reductive elimination , catalysis , cyanation , nickel , nitrile , cobalt , alkyne , organic chemistry , solvent , combinatorial chemistry
A Ni/Co co‐catalyzed reductive hydrocyanation of various alkynes was developed for the production of saturated nitriles. Hydrocyanic acid is generated in situ from safe and readily available formamide. Formamide played multiple roles as a cyano source, dehydrant, and reductant for the Ni II pre‐catalyst and vinyl nitriles, along with acting as the co‐solvent in this reaction. Detailed mechanistic investigation supported a pathway via hydrocyanation of C≡C bond and the subsequent reduction of C=C bond. Wide substrate scope, the employment of a cheap and stable nickel salt as pre‐catalyst, a safe cyano source and convenient experimental operation render this hydrocyanation practical for the laboratory synthesis of saturated nitriles.