Room-Temperature Synthesis of 1,3,5-Tri(<i>het</i>)aryl Benzene from Nitroalkenes Using Pd(OAc)<sub>2</sub>: Complete Mechanistic and Theoretical Studies
Siba P. Midya, Subal Mondal, Abu Saleh Musha Islam, Ambreen Rashid, Sahidul Mondal, Ankan Paul, Pradyut Ghosh
Abstract
Herein, a room-temperature catalytic pathway for 1,3,5-tri(het)aryl derivatives from nitroalkenes using simple Pd(OAc)2 is presented. This newly developed C–C bond-forming methodology takes place in a cascade manner with the initial pallado-Morita–Baylis–Hillman (MBH) type adduct. The broad substrate scopes, functional group tolerance, and different aryl-substituted benzene derivatives make this methodology more attractive. Furthermore, the mechanistic understanding through isolation of intermediates and DFT studies of the catalytic cycle provide requisite insight into the methodology.
Topics & Concepts
ChemistryArylAdductBenzeneCatalysisBenzene derivativesCombinatorial chemistrySubstrate (aquarium)Medicinal chemistryComputational chemistryStereochemistryOrganic chemistryChemical synthesisAlkylBiochemistryOceanographyIn vitroGeologyCatalytic Cross-Coupling ReactionsNanomaterials for catalytic reactionsCatalytic C–H Functionalization Methods