2510-96-5Relevant academic research and scientific papers
Nickel/Cobalt-Catalyzed Reductive Hydrocyanation of Alkynes with Formamide as the Cyano Source, Dehydrant, Reductant, and Solvent
Zhang, Jin,Luo, Cui-Ping,Yang, Luo
, p. 283 - 288 (2020/12/01)
A Ni/Co co-catalyzed reductive hydrocyanation of various alkynes was developed for the production of saturated nitriles. Hydrocyanic acid is generated in situ from safe and readily available formamide. Formamide played multiple roles as a cyano source, dehydrant, and reductant for the NiII pre-catalyst and vinyl nitriles, along with acting as the co-solvent in this reaction. Detailed mechanistic investigation supported a pathway via hydrocyanation of C≡C bond and the subsequent reduction of C=C bond. Wide substrate scope, the employment of a cheap and stable nickel salt as pre-catalyst, a safe cyano source and convenient experimental operation render this hydrocyanation practical for the laboratory synthesis of saturated nitriles. (Figure presented.).
Hydroaminocarbonylation of Alkynes to Produce Primary α,β-Unsaturated Amides Using NH4HCO3 Dually as Ammonia Surrogate and Br?nsted Acid Additive
Wang, Dong-Liang,Guo, Wen-Di,Zhou, Qing,Liu, Lei,Lu, Yong,Liu, Ye
, p. 4264 - 4268 (2018/09/06)
By using NH4HCO3 dually as ammonia surrogate and Br?nsted acid additive, the production of primary α,β-unsaturated amides via hydroaminocarbonylation of alkynes was accomplished efficiently. The advantages of using the solid and inexpensive NH4HCO3 included: (1) the facile and clean manipulation without presence of stinky gaseous NH3 or liquids organic amines, (2) the inhibition of the subsequent dehydration and hydrolysis of amides due to its weak basicity, and (3) the facilitated formation of Pd?H catalytic active species by the released H2CO3 serving as a weak Br?nsted acid additive. In addition, the diphopshine of Dppp with the natural bite angle (βn) of 91° was found indispensable to spur the performance of the palladium catalyst for this reaction. Both terminal and internal phenylacetylene derivatives could be used as the substrates, affording the corresponding primary α,β-unsaturated amides in good yields along with excellent regio-selectivities to the branched ones.
An efficient InCl3-catalyzed hydration of nitriles to amides: acetaldoxime as an effective water surrogate
Kim, Eun Sun,Lee, Hyun Seung,Kim, Sung Hwan,Kim, Jae Nyoung
scheme or table, p. 1589 - 1591 (2010/04/29)
An efficient InCl3-catalyzed hydration protocol of nitriles to amides was developed. The reaction was carried out in toluene at refluxing temperature with the aid of acetaldoxime as an effective water surrogate to produce amides in high yields.
An efficient Pd-catalyzed hydration of nitrile with acetaldoxime
Kim, Eun Sun,Kim, Hoo Sook,Kim, Jae Nyoung
body text, p. 2973 - 2975 (2009/08/09)
An efficient palladium-catalyzed protocol for the hydration of nitrile to amide with acetaldoxime has been developed. A plausible mechanism was suggested involving the first Pd(II)-catalyzed nitrile-oxime coupling and the following disruption of the intermediate into amide and acetonitrile in a concerted manner.
