5633-86-3Relevant academic research and scientific papers
Manganese(I)-Catalyzed H-P Bond Activation via Metal-Ligand Cooperation
Pérez, Juana M.,Postolache, Roxana,Casti?eira Reis, Marta,Sinnema, Esther G.,Vargová, Denisa,De Vries, Folkert,Otten, Edwin,Ge, Luo,Harutyunyan, Syuzanna R.
supporting information, p. 20071 - 20076 (2021/12/03)
Here we report that chiral Mn(I) complexes are capable of H-P bond activation. This activation mode enables a general method for the hydrophosphination of internal and terminal α,β-unsaturated nitriles. Metal-ligand cooperation, a strategy previously not considered for catalytic H-P bond activation, is at the base of the mechanistic action of the Mn(I)-based catalyst. Our computational studies support a stepwise mechanism for the hydrophosphination and provide insight into the origin of the enantioselectivity.
Method for preparing alkenyl cyanide compounds
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Paragraph 0175; 0`176-0178, (2019/10/23)
The invention discloses a method for preparing alkenyl cyanide compounds represented by formula II. Alkynes represented by formula I and a cyanation reagent are subjected to a reduction reaction represented by a formula shown in the description in an organic solvent under the protection of a gas at 20-100 DEG C under the action of a nickel catalyst, a reducing agent and H2O to prepare the alkenyl cyanide compounds represented by formula II. The preparation method of the invention, which adopts the cheap nickel as the catalytic system, has the advantages of simplicity in operation, mild reaction conditions, good compatibility of functional groups, wide application range of the substrate, high reaction efficiency and high yield, so the method has high application and promotion values.
Nickel-Catalyzed Highly Regioselective Hydrocyanation of Terminal Alkynes with Zn(CN)2 Using Water as the Hydrogen Source
Zhang, Xingjie,Xie, Xin,Liu, Yuanhong
supporting information, p. 7385 - 7389 (2018/06/11)
The first efficient and general nickel-catalyzed hydrocyanation of terminal alkynes with Zn(CN)2 in the presence of water has been developed. The reaction provides a regioselective protocol for the synthesis of functionalized vinyl nitriles with a range of structural diversity under mild reaction conditions while obviating use of the volatile and hazardous reagent of HCN. Deuterium-labeling experiments confirmed the role of water as the hydrogen source in this hydrocyanation reaction.
PROCESS FOR HYDROCYANATION OF TERMINAL ALKYNES
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Page/Page column 13; 37, (2018/12/13)
The present invention refers to a process for a Rh-catalyzed Anti-Markovnikov hydrocyanation of terminal alkynes which process discloses, for the first time, the highly stereo- and regio-selective hydrocyanation of terminal alkynes to furnish E- configured alkenyl nitriles and the catalyst used in the present process.
Rh-Catalyzed Anti-Markovnikov Hydrocyanation of Terminal Alkynes
Ye, Fei,Chen, Junting,Ritter, Tobias
supporting information, p. 7184 - 7187 (2017/06/05)
We report the first highly stereo- and regioselective hydrocyanation of terminal alkynes to furnish E-configured alkenyl nitriles. Acrylonitriles can be accessed on gram scale with broad substrate scope and functional group tolerance. The hydrocyanation reaction employs acetone cyanohydrin as a practical alternative to HCN gas.
The Baylis-Hillman chemistry in aqueous media: A convenient synthesis of 2-methylenealkanoates and alkanenitriles
Basavaiah, Deevi,Kumaragurubaran, Nagaswamy
, p. 477 - 479 (2007/10/03)
A convenient, general and efficient synthesis of 2-methylenealkanoates and alkanenitriles is accomplished via the regioselective nucleophilic (SN2′) addition of hydride ion from NaBH4 to (2Z)-2-(bromomethyl)alk-2-enoates and 2-(bromomethyl)alk-2-enenitriles respectively in the presence of DABCO in environment friendly aqueous media. Synthesis of two hypoglycemic agents is also described.
A simple and regioselective conversion of terminal acetylene into 2-substituted acrylonitrile
Luo, Fen-Tair,Ko, Sheng-Li,Chao, Dean-Yang
, p. 8061 - 8062 (2007/10/03)
Treatment of terminal acetylene with in situ generated hydrogen iodide and followed by the reaction with cuprous cyanide provided a simple and regioselective transformation of acetylene into 2-substituted acrylonitrile in fair to good yields.
A New Simple Synthesis of α-Substituted Acrylonitriles
Baraldi, P. G.,Pollini, G. P.,Zanirato, V.,Barco, A.,Benetti, S.
, p. 969 - 970 (2007/10/02)
An efficient preparation of α-substituted acrylonitriles 6 based on the utilization of 4-cyano-3-ketothiolane enolate anion (3) as a synthetic equivalent to α-acrylonitrile anion (1) is described.
The Stereochemistry of Organometallic Compounds. XXIV. Nickel(0)-Catalysed Additions of Hydrogen Cyanide to Alkynes
Jackson, W. Roy,Lovel, Craig G.
, p. 1975 - 1982 (2007/10/02)
Hydrogen cyanide will add to alkynes bearing a wide range of substituents with cis stereospecificity, high regioselectivity, and in moderate-to-good yields, when the reaction is catalysed by tetrakis-(triphenyl phosphite)nickel(0).
