121054-03-3Relevant articles and documents
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Vedejs,E.,Telschow,J.E.
, p. 740 - 741 (1976)
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Ionic liquid [omim][PF6] as an efficient and recyclable reaction media for the cyanosilylation of aldehydes without Lewis acid or any special activation
Shen, Zhi-Liang,Ji, Shun-Jun,Loh, Teck-Peng
, p. 3137 - 3139 (2005)
Ionic liquid [omim][PF6] has been demonstrated as an efficient and environmentally friendly reaction media as well as a promoter for the cyanosilylation of aldehydes under mild conditions. In addition, the recovered ionic liquid could be reused for subsequent runs with only a gradual decrease in activity.
Nickel-Catalyzed, Reductive C(sp3)?Si Cross-Coupling of α-Cyano Alkyl Electrophiles and Chlorosilanes
Oestreich, Martin,Zhang, Liangliang
supporting information, 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.
Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents
Donslund, Aske S.,Neumann, Karoline T.,Corneliussen, Nicklas P.,Grove, Ebbe K.,Herbstritt, Domenique,Daasbjerg, Kim,Skrydstrup, Troels
supporting information, p. 9856 - 9860 (2019/07/09)
Herein, we report a nickel-catalyzed carbonylative coupling of α-bromonitriles and alkylzinc reagents with near stoichiometric carbon monoxide to give β-ketonitriles in good yields. The reaction is catalyzed by a readily available and stable nickel(II) pincer complex. The developed protocol tolerates substrates bearing a variety of functional groups, which would be problematic or incompatible with previous synthetic methods. Additionally, we demonstrate the suitability of the method for carbon isotope labeling by the synthesis of 13C-labeled β-ketonitriles and their transformation into isotopically labeled heterocycles.