87639-24-5Relevant academic research and scientific papers
Photo-Promoted Decarboxylative Alkylation of α, β-Unsaturated Carboxylic Acids with ICH2CN for the Synthesis of β, γ-Unsaturated Nitriles
Pan, Chunxiang,Yang, Chunhui,Li, Kangkui,Zhang, Keyang,Zhu, Yuanbin,Wu, Shiyuan,Zhou, Yongyun,Fan, Baomin
supporting information, p. 7188 - 7193 (2021/10/01)
An efficient, catalyst/photocatalyst-free, and cost-effective methodology for the decarboxylative alkylation of α,β-unsaturated carboxylic acids to synthesize β,γ-unsaturated nitriles has been developed. The reaction proceeded in an environmentally benign atmosphere of blue light-emitting diode irradiation with K2CO3 and water at room temperature. The methodology worked for a wide range of substrates (22 examples) with up to 83% yield. The protocol is also compatible for gram-scale synthesis.
Visible light-induced palladium-catalyzed ring opening β-H elimination and addition of cyclobutanone oxime esters
Xing, Wei-Long,Shang, Rui,Wang, Guang-Zu,Fu, Yao
supporting information, p. 14291 - 14294 (2019/12/02)
A palladium catalyst under visible light irradiation activates cyclobutanone oxime ester through single electron transfer to induce radical ring opening to generate hybrid cyanoalkyl Pd(i) radical species. Hybrid cyanoalkyl Pd(i) radical species can undergo either β-H elimination to deliver (E)-4-arylbut-3-enenitrile or undergo radical addition with silyl enol ether and enamide to generate δ-cyano ketones. A dual ligand system composed of two phosphine ligands is essential for the high reactivity.
Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters
Michel, Nicholas W. M.,Jeanneret, Alexandria D. M.,Kim, Hyehwang,Rousseaux, Sophie A. L.
, p. 11860 - 11872 (2018/10/02)
A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)2. Alkene additives were found to inhibit catalysis, suggesting that avoiding β-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (±)-naproxen from commercially available starting materials.
Free-Radical-Promoted Copper-Catalyzed Decarboxylative Alkylation of α,β-Unsaturated Carboxylic Acids with ICH2CF3 and Its Analogues
Zhu, Yan,Gong, Juwen,Wang, Yonghui
, p. 7428 - 7436 (2017/07/26)
A novel and efficient free-radical-promoted copper-catalyzed decarboxylative alkylation of α,β-unsaturated carboxylic acids with ICH2CF3 and its analogues has been developed. This methodology provides a convenient access to the synthesis of allylic trifluoromethyl and β-CF3 ketone containing compounds as well as other biologically useful fluorinated molecules and materials.
Organotin Nucleophiles. 5. Palladium-Catalyzed Allylic Propargylation with Allenylstannane
Keinan, Ehud,Peretz, Moshe
, p. 5302 - 5309 (2007/10/02)
Allenyltrialkylstannanes were found to react with various allylic acetates in the presence of catalytic amounts of Pd(PPh3)4 under mild neutral conditions, providing a novel approach for obtaining the 1,5-enyne carbon skeleton.The regioselectivity of propargylation depends largely on the electron-withdrawing properties of the substituents at the two ends of the allylic system: substitution occurs at the end of closer proximity to the more electronegative group.Allylic cyanohydrin acetates are substituted at a position α to the cyano group along with formation of a reduced side product.Several mechanistic aspects of these reactions are discussed.
