23226-12-2Relevant academic research and scientific papers
Cyanomethylation of alkenes with C-H bond activation of acetonitrile: In situ generated diazonium salts as promoters without transition-metals
Ni, Zhangqin,Huang, Xin,Wang, Jichao,Pan, Yuanjiang
, p. 522 - 526 (2015)
Diazonium salts, which were in situ generated from p-anisidine and tert-butyl nitrite, could be used as a novel radical promoter for the Csp3-H functionalization of acetonitrile. The cyanomethylation of alkenes could be performed wit
Heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile: Synthesis of diverse nitrogenous heterocyclic compounds
Pan, Guanglong,Yang, Qian,Wang, Wentao,Tang, Yurong,Cai, Yunfei
supporting information, p. 1171 - 1180 (2021/05/27)
A visible light-mediated heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile has been established using K-modified carbon nitride (CN-K) as a recyclable semiconductor photocatalyst. This protocol, employing readily accessible al
Photochemical generation of radicals from alkyl electrophiles using a nucleophilic organic catalyst
Schweitzer-Chaput, Bertrand,Horwitz, Matthew A.,de Pedro Beato, Eduardo,Melchiorre, Paolo
, p. 129 - 135 (2018/12/13)
Chemists extensively use free radical reactivity for applications in organic synthesis, materials science, and life science. Traditionally, generating radicals requires strategies that exploit the bond dissociation energy or the redox properties of the precursors. Here, we disclose a photochemical catalytic approach that harnesses different physical properties of the substrate to form carbon radicals. We use a nucleophilic dithiocarbamate anion catalyst, adorned with a well-tailored chromophoric unit, to activate alkyl electrophiles via an SN2 pathway. The resulting photon-absorbing intermediate affords radicals upon homolytic cleavage induced by visible light. This catalytic SN2-based strategy, which exploits a fundamental mechanistic process of ionic chemistry, grants access to open-shell intermediates from a variety of substrates that would be incompatible with or inert to classical radical-generating strategies. We also describe how the method’s mild reaction conditions and high functional group tolerance could be advantageous for developing C–C bond-forming reactions, for streamlining the preparation of a marketed drug, for the late-stage elaboration of biorelevant compounds and for enantioselective radical catalysis.
Visible-Light-Promoted Oxidative Alkylarylation of N-Aryl/Benzoyl Acrylamides Through Direct C?H Bond Functionalization
Lu, Maojian,Zhang, Tao,Tan, Dabao,Chen, Chengzhu,Zhang, Ying,Huang, Mingqiang,Cai, Shunyou
supporting information, p. 4237 - 4242 (2019/08/16)
Radical cascade oxidative alkylarylations of N-aryl/benzoyl acrylamides have been established through visible-light-enabled photocatalysis, furnishing a wide variety of functionalized oxindoles and isoquinolinediones in good-to-excellent yields under the
Fe-promoted radical cyanomethylation/arylation of arylacrylamides to access oxindoles via cleavage of the sp3 C-H of acetonitrile and the sp2 C-H of the phenyl group
Pan, Changduo,Zhang, Honglin,Zhu, Chengjian
supporting information, p. 361 - 364 (2015/02/05)
Radical cyanomethylation/arylation of arylacrylamides to access oxindoles with acetonitrile as the radical precursor is described. This reaction involves dual C-H bond functionalization, including the sp3 C-H of acetonitrile and the sp2/s
Palladium-catalyzed oxidative arylalkylation of activated alkenes: Dual C-H bond cleavage of an arene and acetonitrile
Wu, Tao,Mu, Xin,Liu, Guosheng
supporting information; experimental part, p. 12578 - 12581 (2012/02/04)
Not one but two: The title reaction proceeds through the dual C-H bond cleavage of both aniline and acetonitrile (see scheme). The reaction affords a variety of cyano-bearing indolinones in excellent yield. Mechanistic studies demonstrate that this reaction involves a fast arylation of the olefin and a rate-determining C-H activation of the acetonitrile. Copyright
