18748-59-9Relevant academic research and scientific papers
Regio-controllable Cobalt-Catalyzed Sequential Hydrosilylation/Hydroboration of Arylacetylenes
Cheng, Zhaoyang,Guo, Jun,Lu, Zhan,Sun, Yufeng,Zheng, Yushan,Zhou, Zhehong
, p. 22454 - 22460 (2021)
Regiodivergent addition reactions provide straightforward and atom-economic approaches to access different regioisomers. However, the regio-chemistry control to access all the possible results is still challenging especially for the reaction involving multiple addition steps. Herein, we reported regio-controllable cobalt-catalyzed sequential hydrosilylation/hydroboration of arylacetylenes, delivering all the possible regio-outcomes with high regioselectivities (up to >20/1 rr for all the cases). Each regioisomer of value-added silylboronates could be efficiently and regioselectively obtained from the same materials. The adjustment of the ligands of cobalt catalysts combined with dual catalysis relay strategy is the key to achieve regio-chemistry control. This regio-controllable research might inspire the exploration of the diversity-oriented synthesis that involves multiple additions and provide full sets of regioisomers of other synthetic useful molecules.
THE PREPARATION AND CHEMISTRY OF (R)-(1-NAPHTYL)PHENYLMETHYLSILYLMETHYLLITHIUM: STEREOCHEMISTRY AT SILICON IN THE ELIMINATION OF β-HYDROXYSILANES
Larson, Gerald L.,Prieto, J. Antonio,Ortiz, Edgardo
, p. 3781 - 3790 (2007/10/02)
(R)-(1-naphthyl)phenylmethylsilylmethyllithium has been prepared from 1-naphthylphenylmethylsilylmethyltri-n-butyltin, which is in turn prepared in four steps from (R)-(1-naphthyl)phenylmethylsilane.The title lithium reagent was reacted with benzaldehyde, pivaldehyde, acrolein and 2-methylcyclohexanone to produce the corresponding β-hydroxysilanes in good yield, but with only a 3-4percent diastereomeric excess.Unfortunately, these diastereomers proved impossible to separate.Model studies employing the methyldiphenylsilyl group showed that these β-hydroxysilanes could be protiodesilylated to give the corresponding methyl alcohol.The products from the adduct with pivaldehyde and acrolein were used to investigate the stereochemistry at silicon of the β-hydroxysilanes.This was found to occur with inversion of configuration at silicon when the elimination is carried out with boron fluoride etherate, sulfuric acid or acetic acid/sodium acetate, but with retention of configuration when carried out with potassium hydride.
