Cu-catalyzed debrominative cyanation of gem-dibromoolefins: a facile access to α,β-unsaturated nitriles.
An efficient catalytic route for the synthesis of α,β-unsaturated nitriles from easily accessible gem-dibromoolefins has been developed. The method utilized inexpensive reagents such as Cu2O as a catalyst, L-proline as a ligand and NaCN as a cyanide source to afford α,β-unsaturated nitriles in high yields (62-86%). A deuterium exchange study has shown that one of the bromide atoms of gem-dibromoolefins exchanges with cyanide while the other with a deuterium atom.
National Chemical Laboratory, Chemical Engineering & Process Development Division, Pune 411008, Maharastra, India. a.sudalai@ncl.res.in.
Brij Bhushan
BB
Ahuja
Arumugam
A
Sudalai
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry; D054879:Halogenation; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D003486:Cyanides; D009570:Nitriles; D003300:Copper; D011392:Proline