Efficient nickel-catalyzed hydrocyanation of alkenes using acetone cyanohydrin as a safer cyano source

[Display omitted] •An efficient and safer hydrocyanation reaction.•An active Ni(0) catalyst prepared in situ.•Good functional group tolerance.•A few insights into the roles of catalyst system. An active nickel catalyst prepared in situ from a Ni(II) compound, phosphine ligand, and zinc powder was fo...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 57; no. 29; pp. 3199 - 3203
Main Authors Nemoto, Koji, Nagafuchi, Tsuyoshi, Tominaga, Ken-ichi, Sato, Kazuhiko
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 20.07.2016
Elsevier
Subjects
Alkene
Chemistry
Chemistry, Organic
Cyanohydrin
Hydrocyanation
Nickel catalyst
Physical Sciences
Science & Technology
Nickel catalyst
Alkene
Hydrocyanation
Cyanohydrin
ASYMMETRIC HYDROCYANATION
COMPLEXES
ISOMERIZATION
CYANATION
ALPHA,BETA-UNSATURATED AMIDES
CN
NORBORNADIENE
LIGANDS
CHLOROARENES
HYDROGEN-CYANIDE
Online AccessGet full text

Cover

More Information
Summary:[Display omitted] •An efficient and safer hydrocyanation reaction.•An active Ni(0) catalyst prepared in situ.•Good functional group tolerance.•A few insights into the roles of catalyst system. An active nickel catalyst prepared in situ from a Ni(II) compound, phosphine ligand, and zinc powder was found to be an efficient catalyst system for the hydrocyanation of various alkenes using acetone cyanohydrin as a safer cyano source. The combination of NiCl2·6H2O and 1,3-bis(diphenylphosphino)propane was the most efficient catalyst precursor in DMF. Under the optimized conditions, various styrenes, heterocyclic alkenes, and aliphatic alkenes were converted to their corresponding nitriles in excellent yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.06.036