title: Rh(III)-catalyzed decarboxylative coupling of acrylic acids with unsaturated oxime esters: carboxylic acids serve as traceless activators.
abstract: α,β-Unsaturated carboxylic acids undergo Rh(III)-catalyzed decarboxylative coupling with α,β-unsaturated O-pivaloyl oximes to provide substituted pyridines in good yield. The carboxylic acid, which is removed by decarboxylation, serves as a traceless activating group, giving 5-substituted pyridines with very high levels of regioselectivity. Mechanistic studies rule out a picolinic acid intermediate, and an isolable rhodium complex sheds further light on the reaction mechanism.
authors: Department of Chemistry, Colorado State University , Fort Collins, Colorado 80523, United States.
authors: Jamie M
authors: JM
authors: Neely
authors: Tomislav
authors: T
authors: Rovis
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D010091:Oximes / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000179:Acrylates; D002264:Carboxylic Acids; D004952:Esters; D010091:Oximes; D012238:Rhodium; C036658:acrylic acid