1360735-28-9Relevant academic research and scientific papers
Rh(III)-catalyzed decarboxylative coupling of acrylic acids with unsaturated oxime esters: Carboxylic acids serve as traceless activators
Neely, Jamie M.,Rovis, Tomislav
, p. 2735 - 2738 (2014/03/21)
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.
Rh(III)-catalyzed regioselective synthesis of pyridines from alkenes and α,β-unsaturated oxime esters
Neely, Jamie M.,Rovis, Tomislav
, p. 66 - 69 (2013/02/23)
α,β-Unsaturated O-pivaloyl oximes are coupled to alkenes by Rh(III) catalysis to afford substituted pyridines. The reaction with activated alkenes is exceptionally regioselective and high-yielding. Mechanistic studies suggest that heterocycle formation proceeds via reversible C-H activation, alkene insertion, and a C-N bond formation/N-O bond cleavage process.
Synthesis of pyridines from ketoximes and terminal alkynes via C-H bond functionalization
Martin, Rhia M.,Bergman, Robert G.,Ellman, Jonathan A.
experimental part, p. 2501 - 2507 (2012/05/05)
An expedient one-pot rhodium catalyzed C-H bond functionalization/ electrocyclization/dehydration procedure has been developed for the synthesis of highly substituted pyridine derivatives from terminal alkynes and α,β-unsaturated ketoximes. The use of electron-deficient phosphite ligands is important to suppress dimerization of the terminal alkynes to enynes.
