13312-99-7Relevant academic research and scientific papers
Electrophilic cyanation of allylic boranes: Synthesis of β,γ-unsaturated nitriles containing allylic quaternary carbon centers
Kiyokawa, Kensuke,Hata, Shotaro,Kainuma, Shunpei,Minakata, Satoshi
supporting information, p. 458 - 461 (2019/01/10)
The electrophilic cyanation of allylic boranes, a process that is applicable to the construction of allylic quaternary carbon centers, is reported. The reaction has a broad substrate scope with a high functional group tolerance. The results represent an u
Indium Tribromide Catalyzed Coupling Reaction of Enol Ethers with Silyl Ketene Imines toward the Synthesis of β,γ-Unsaturated Nitriles
Nishimoto, Yoshihiro,Nishimura, Takashi,Yasuda, Makoto
supporting information, p. 18301 - 18308 (2015/12/24)
Herein, a coupling reaction of enol ethers with silyl ketene imines in the presence of catalytic amounts of InBr3 and Me3SiBr is described. Kinetic studies have revealed that an indium catalyst and Me3SiBr accelerated the coupling process and the regeneration of the catalyst, respectively. Various types of enol ethers and silyl ketene imines are applicable. In addition, a formal synthesis of verapamil was achieved by using this novel coupling reaction. Let's get together: The coupling reaction of enol ethers with silyl ketene imines in the presence of a catalytic amount of InBr3 and Me3SiBr is shown (see scheme, TBS=tert-butyl dimethylsilyl). Kinetic studies revealed that an indium salt and Me3SiBr accelerated the coupling process and the regeneration of the catalyst. Several enol ethers and silyl ketene imines are applicable to this strategy.
Cesium hydroxide: A superior base for the catalytic alkynylation of aldehydes and ketones and catalytic alkenylation of nitriles
Tzalis, Dimitrios,Knochel, Paul
, p. 1463 - 1465 (2007/10/03)
The efficient addition of terminal alkynes to aldehydes or ketones to give propargyl alcohols in yields of 66-96% can be achieved by activation with catalytic amounts of CsOH · H2O [Eq.(a)]. A CsOH-catalyzed addition of acetonitrile derivatives
New Syntheses of Isomerically Pure Allyl and Propargyl Cyanides by Isocyanide-Cyanide Rearrangement
Wolber, Erwin K. A.,Schmittel, Michael,Ruechardt, Christoph
, p. 525 - 532 (2007/10/02)
A new route for the synthesis of isomerically pure allyl and propargyl cyanides has been developed.Allylic amines are synthesized from the corresponding alcohols by Mitsunobu or by Overman reaction.Formylation with formic acid derivatives provides N-substituted formamides, which are dehydrated to isocyanides. 1,2-Sigmatropic rearrangement by flash pyrolysis provides the isomerically pure allyl and propargyl cyanides. Key Words: Isocyanide-cyanide rearrangment / Cyanides, allyl- and propargyl-
