Computational Mechanistic Study of Stereoselective Suzuki Coupling of an α-Cyano-Activated Secondary Alkyl
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https://figshare.com/articles/dataset/Computational_Mechanistic_Study_of_Stereoselective_Suzuki_Coupling_of_an_Cyano_Activated_Secondary_Alkyl/2511400
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资源简介：
Palladium-catalyzed cross-couplings of secondary alkyls
are promising
tools for the stereoselective formation of carbon–carbon bonds.
We report a computational mechanistic study of the stereoselective
Suzuki coupling between (S)-2-chloropropanenitrile
and phenylboronic acid, following a recent experimental report on
related α-cyanohydrin triflates (J. Am. Chem. Soc. 2010, 132, 2524). Added Lewis base helps accelerate
SN2 oxidative addition, leading to the experimentally observed
inversion of configuration. Undesired β-hydride elimination
side reactions are reduced by the activating cyano group’s
inductive effects, by cyano-PdII coordination, and by excess
boronic acid. The catalyst ligand’s trans influence and steric
bulk also affect the rate of β-hydride elimination, suggesting
design rules for alkyl cross-coupling ligands.
创建时间：
2016-02-20
