1209495-04-4Relevant academic research and scientific papers
Nickel-Catalyzed, Reductive C(sp3)?Si Cross-Coupling of α-Cyano Alkyl Electrophiles and Chlorosilanes
Oestreich, Martin,Zhang, Liangliang
, p. 18587 - 18590 (2021/07/25)
A nickel/zinc-catalyzed cross-electrophile coupling of alkyl electrophiles activated by an α-cyano group and chlorosilanes is reported. Elemental zinc is the stoichiometric reductant in this reductive coupling process. By this, a C(sp3)?Si bond can be formed starting from two electrophilic reactants whereas previous methods rely on the combination of carbon nucleophiles and silicon electrophiles or vice versa.
Mild Base Promoted Nucleophilic Substitution of Unactivated sp3-Carbon Electrophiles with Alkenylboronic Acids
Liu, Shiwen,Zeng, Xiaojun,Hammond, Gerald B.,Xu, Bo
supporting information, p. 3667 - 3671 (2018/09/12)
Diverse alkenylboronic acids react smoothly with various sp3-carbon electrophiles such as unactivated alkyl triflates in the presence of mild bases such as K3PO4. The reaction protocol is very mild and thereby enables high functional group tolerance. This transition metal-free condition is orthogonal towards the classic transition metal catalyzed Suzuki coupling. (Figure presented.).
Copper-Catalyzed Substitution of α-Triflyloxy Nitriles and Esters with Silicon Nucleophiles under Inversion of the Configuration
Scharfbier, Jonas,Hazrati, Hamideh,Irran, Elisabeth,Oestreich, Martin
, p. 6562 - 6565 (2017/12/26)
A copper-catalyzed nucleophilic displacement of α-triflyloxy nitriles and esters with silicon nucleophiles allows for the stereospecific generation of highly enantioenriched α-silylated carboxyl compounds. The enantioselective synthesis of α-silylated nitriles is unprecedented. The catalytic system exhibits good functional group tolerance. The stereochemical course of the substitution is shown to proceed with inversion of the configuration. The new reaction is an addition to the still limited number of methods for catalytic C(sp3)-Si cross-coupling.
