Theoretical study of Sonogashira reactions on the formation mechanism ofseveral p-carborane compounds

Cross-coupling is one of the most significant and extensively utilized methods in chemistryfor linking two organic substrates using a metal catalyst. In this method, two active groups (suchas aryl or alkyl) are connected to each other via an alkyl radical or another reactive group. Thepalladium-catalyzed Sonogashira reaction [۱-۳] is one of the most important and widely usedmethods for preparing arylacetylenes and conjugated enynes, which are precursors for naturalproducts, pharmaceuticals, and materials with specialized optical and electronic properties. Thegeneral Sonogashira protocol for coupling terminal alkynes with aryl or alkenyl halides (ortriflates) typically involves an organic solvent, a Pd(۰)/Cu(I) catalytic system, and at least astoichiometric amount of a base (Scheme ۱). Herein, we have investigated the feasibility ofobtaining heteroaryl derivatives of carboranes through Pd-catalyzed B–C cross-couplingreactions involving various organozinc heterocycle. The molecular structures of the compoundsstudied here, such as reactants, transition states, intermediates and products, have been optimizedusing the Cam-B۳LYP-D۳ method in conjunction with the def۲-SVP in solution. The Gaussian۰۹ (revision-D) program package is used for all quantum mechanical calculations. Based on theoptimized structures obtained during the solution process,single point energies are determinedusing the IEF-PCM of the CamB۳LYP-D۳/def۲-TZVP//Cam-B۳LYP-D۳/def۲-SVP theoreticallevel. As seen in.

کلیدواژه ها:

Cross-coupling reactions ، Sonogashira reaction ، DFT calculations ، Palladium