The mechanism and origin of selectivities for NHC-catalyzed synthesis of axially chiral benzothiophene/benzofuran-fused biaryls
Jiaming Zhang, Qinyu Qiao, Zhou-Jie Wu, Zhou Pang, Qianqian Shi, Yanyan Wang, Yan Qiao, Donghui Wei
Abstract
, and (8) transformation to axial chirality. Moreover, the calculated results can reasonably explain the observed chemo- and stereoselectivities for the formation of both benzothiophene/benzofuran-fused biaryls in these kinds of reactions. Further non-covalent interaction (NCI) and atoms-in-molecules (AIM) analyses demonstrate that the hydrogen bond interactions are responsible for the stability of key stereoselective transition states. This work would be useful for understanding the origin of stereoselectivity of NHC-catalyzed intermolecular cyclization reactions for the synthesis of axially benzothiophene/benzofuran-fused biaryl compounds.
Topics & Concepts
BenzothiopheneBenzofuranCatalysisChemistryIntermolecular forceOrganic chemistryComputational chemistryCombinatorial chemistryStereochemistryMoleculeThiopheneAxial and Atropisomeric Chirality SynthesisSynthesis and Properties of Aromatic CompoundsAsymmetric Synthesis and Catalysis