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Catalytic Hydration of Benzonitrile and Acetonitrile using Nickel(0)
Author(s) -
Crestani Marco G.,
Arévalo Alma,
García Juventino J.
Publication year - 2006
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.200505382
Subject(s) - chemistry , benzonitrile , acetamide , catalysis , nitrile , acetonitrile , benzamide , nickel , acetanilide , homogeneous catalysis , medicinal chemistry , inorganic chemistry , photochemistry , organic chemistry
Abstract The homogeneous catalytic hydration of benzo‐ and acetonitrile under thermal conditions was achieved using nickel(0) compounds of the type [(dippe)Ni(η 2 ‐NCR)] with R=phenyl or methyl (compounds 1 and 2 , respectively), as the specific starting intermediates. Alternatively, the complexes may be prepared in situ by direct reaction of the precursor [(dippe)NiH] 2 ( 3 ) with the respective nitrile. Hydration appears to occur homogeneously, as tested by mercury drop experiments, producing benzamide and acetamide, respectively. Addition of Bu 4 NI did not lead to catalysis inhibition, suggesting the prevalence of Ni(0) intermediates during catalysis. Hydration using analogous complexes of 3 , such as [(dtbpe)NiH] 2 ( 4 ) and [(dcype)NiH] 2 ( 5 ) was also addressed.