Pd-catalyzed bicyclization of 2-alkynylhalobenzenes and propargylic alcohols for the formation of indeno[1,2]furans: a DFT study

The mechanism of palladium-catalyzed bicyclization of 2-alkynylhalobenzenes and propargylic alcohols for the formation of indeno[1,2]furans has been studied computationally with the aid of density functional theory (DFT). Full free energy profiles are computed for different reaction equations between different reaction substrates. The calculation results showed that the catalytic cycle is found to contain six steps, oxidative addition, ligand substitution, first CC triple bond insertion, rearrangement, second CC triple bond insertion and reductive elimination, with the reductive elimination being the rate-determining step for the different reaction equations (1), (2) and (3). Our calculations are consistent with experimental observations. Copyright (c) 2014 John Wiley & Sons, Ltd.