110327-47-4Relevant academic research and scientific papers
Pyrenedione-Catalyzed α-Olefination of Nitriles under Visible-Light Photoredox Conditions
Bains, Amreen K.,Ankit, Yadav,Adhikari, Debashis
supporting information, p. 2019 - 2023 (2021/04/05)
Herein, we report a combination of pyrenedione (PD) and KOtBu to achieve facile alcohol dehydrogenation under visible-light excitation, where aerobic oxygen is utilized as the terminal oxidant. The resulting carbonyl compound can be easily converted to vinyl nitriles in a single-pot reaction, at 60 °C in 6-8 h. This environmentally benign, organocatalytic approach has distinct advantages over transition-metal-catalyzed α-olefination of nitriles, which often operate at a significantly higher temperature for an extended reaction time.
Solvent-free condensation of arylacetonitrile with aldehydes
Guillot, Régis,Loupy, André,Meddour, Abdelkrim,Pellet, Michèle,Petit, Alain
, p. 10129 - 10137 (2007/10/03)
The condensation of a series of arylacetonitriles with aldehydes can be carried out by mixing equivalent amounts of reagents with neat powdered KOH at room temperature for 3-60 min depending on the aldehyde steric hindrance. At higher temperature (110°C), yields were generally higher and purity increased within very short reaction times (1-5 min). With pentamethylphenylacetonitrile, a phase transfer agent was necessary to give a satisfactory yield.
Direct Synthesis of α,β-Unsaturated Nitriles Catalyzed by Nonionic Superbases
D'Sa, Bosco A.,Kisanga, Philip,Verkade, John G.
, p. 3961 - 3967 (2007/10/03)
We report herein the use of 3-30 mol % of a new class of tricyclic strong nonionic Lewis bases P(MeNCH2CH2)3N and P(HNCH2CH2)(i-PrNCH2CH2) 2N for the direct catalytic synthesis of a variety of functionalized α,β-unsaturated nitriles in high yields from aldehydes and acetonitrile or benzyl cyanide at 40-50°C. Evidence for a novel mechanistic pathway proposed for this reaction in a polar protic solvent such as methanol, and a nonpolar aprotic solvent such as benzene is also presented. Under these conditions, primary and secondary aliphatic aldehydes do not condense satisfactorily with acetonitrile to give the α,β-unsaturated nitrile, and ketones do not condense with either benzyl cyanide or acetonitrile.
