Room-Temperature Synthesis of 1,3,5-Tri(het)aryl Benzene from Nitroalkenes Using Pd(OAc)2: Complete Mechanistic and Theoretical Studies

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.

Automated summary

Here, we present a room-temperature catalytic pathway for the synthesis of 1,3,5-tri(het)aryl derivatives from nitroalkenes using simple Pd(OAc)(2). This newly developed method forms C-C bonds in a cascade manner starting from a pallado-Morita-Baylis-Hillman (MBH) type adduct. The broad substrate scopes, functional group tolerance, and different aryl-substituted benzene derivatives make this method more attractive. Furthermore, the isolation of intermediates and DFT studies provide important insights into the mechanism of the catalytic cycle.