20068-10-4Relevant academic research and scientific papers
Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes
Hu, Dandan,Liu, Jiayue,Ren, Hongjun,Song, Jinyu,Zhang, Jun-Qi,Zhu, Guorong
supporting information, p. 786 - 790 (2022/01/28)
A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti
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.
Cu-Catalyzed atom transfer radical addition reactions of alkenes with α-bromoacetonitrile
Pu, Weiya,Sun, Dani,Fan, Wanyue,Pan, Wenwen,Chai, Qinghui,Wang, Xiaoxing,Lv, Yunhe
supporting information, p. 4821 - 4824 (2019/05/02)
A practical, simple, and efficient copper-catalyzed atom transfer radical addition reaction of alkenes with α-bromoacetonitrile is realized. With this methodology, various γ-bromonitriles and β,γ-unsaturated nitriles were efficiently constructed.
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.
Synthesis method of (E)-4-aryl-3-butenonitrile compound
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Paragraph 0050; 0051; 0052, (2019/04/29)
The invention belongs to the technical field of organic synthesis chemistry, and discloses a synthesis method of a (E)-4-aryl-3-butenonitrile compound. According to the method, under catalysis of copper iodide, a target compound is synthesized in one step
From isonitrile to nitrile via ketenimine intermediate: Palladium-catalyzed 1,1-carbocyanation of allyl carbonate by α-isocyanoacetate
Qiu, Guanyinsheng,Sornay, Charlotte,Savary, David,Zheng, Sheng-Cai,Wang, Qian,Zhu, Jieping
, p. 6966 - 6971 (2018/11/03)
A palladium-catalyzed 1,1-carbocyanation of allyl carbonate by α-quaternary α-isocyanoacetate was developed. Formation of ketenimine followed by homolysis of the C–N bond and recombination of the resulting caged radical pair was proposed to account for the formation of the unusual coupling product, the β-cyano-γ,δ-unsaturated ester.
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.
Transforming Olefins into γ,δ-Unsaturated Nitriles through Copper Catalysis
Wu, Xuesong,Riedel, Jan,Dong, Vy M.
supporting information, p. 11589 - 11593 (2017/09/11)
We have developed a strategy to transform olefins into homoallylic nitriles through a mechanism that combines copper catalysis with alkyl nitrile radicals. The radicals are easily generated from alkyl nitriles in the presence of the mild oxidant di-tert-butyl peroxide. This cross-dehydrogenative coupling between simple olefins and alkylnitriles bears advantages over the conventional use of halides and toxic cyanide reagents. With this method, we showcase the facile synthesis of a flavoring agent, a natural product, and a polymer precursor from simple olefins.
Copper-Catalyzed Regioselective Allylic Cyanation of Allylic Compounds with Trimethylsilyl Cyanide
Munemori, Daisuke,Tsuji, Hiroaki,Uchida, Kenta,Suzuki, Tomoaki,Isa, Kazuki,Minakawa, Maki,Kawatsura, Motoi
, p. 2747 - 2750 (2015/10/28)
The copper-catalyzed regioselective allylic cyanation of allylic compounds with trimethylsilyl cyanide (TMSCN) is described. Copper(I) iodide (CuI), copper(I) cyanide (CuCN) and copper(II) chloride (CuCl2) are shown to effectively catalyze the cyanation of various allylic substrates to afford the corresponding allylic cyanides in good yields and high regioselectivities. The reaction in the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO) reveals that the cyanation proceeds via a radical pathway.
