Mechanistic Analysis of Alkyne Haloboration: A DFT, MP2, and DLPNO-CCSD(T) Study.

ABSTRACT: Stereocontrol of the alkyne haloboration reaction has received attention in many experimental but few theoretical studies. Here we present a detailed quantum-chemical study of mechanisms leading to Z versus E isomers of haloboration products, considering acetylene and propyne combined with BCl₃, BBr₃, and BI₃. Calculations using B3LYP-D3, MP2, and DLPNO-CCSD(T) methods are used to study polar reactions between the alkyne and BX₃ in the absence and presence of an additional halide anion whose content in the reaction mixture can be controlled experimentally. The formation of anti-haloboration products via radical mechanisms is also explored, namely, by adding BX₃ to (Z)-halovinyl radical. For the anti-h

SUBMITTER: Stosek J 

PROVIDER: S-EPMC10405270 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature