Nickel-catalyzed synthesis of acrylamides from alpha-olefins and isocyanates.
[reaction: see text] The nickel(0)-catalyzed coupling of alpha-olefins and isocyanates proceeds in the presence of the N-heterocyclic carbene ligand IPr to provide alpha,beta-unsaturated amides. Carbon-carbon bond formation occurs preferentially at the 2-position of the olefin. The N-tert-butyl amide products can be converted to the corresponding primary amides under acidic conditions.
Schleicher
Kristin D
KD
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Jamison
Timothy F
TF
D000178:Acrylamides / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry; D017953:Isocyanates / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*
D000178:Acrylamides; D000475:Alkenes; D000577:Amides; D005030:Ethylenes; D017953:Isocyanates; D009532:Nickel; C036216:ethylene