34136-59-9Relevant academic research and scientific papers
Incorporation of Carbon Dioxide into Carbamate Directing Groups: Palladium-Catalyzed meta-C–H Olefination and Acetoxylation of Aniline Derivatives
Yang, Long,Fu, Lei,Li, Gang
, p. 2235 - 2240 (2017)
Carbon dioxide (CO2), a readily available, non-toxic, and inexpensive greenhouse gas, is an ideal reagent for carbamate synthesis. For the first time, CO2 has been efficiently incorporated into a novel nitrile-containing directing group (DG) for meta-C–H activation of anilines under mild conditions. Thus, various aniline derivatives were meta-olefinated with palladium(II) acetate. meta-C–H acetoxylation was also feasible and the carbamate DG could be easily removed under basic conditions. The practicality of substrate preparation, functional group tolerance, and versatility of this method make it a valuable addition to the meta-C–H functionalization of anilines. (Figure presented.).
Synthesis of 2-Substituted 3-Alkylidene-2,3-dihydro-1H-isoindol-1-imines through cyclization of [1-(2-Cyanophenyl)alkylidene]aminide intermediates generated from the reaction of 2-(1-Azidoalkyl)benzonitriles with NaH
Kobayashi, Kazuhiro,Ezaki, Kosuke,Nozawa, Ippei
, p. 1624 - 1629 (2014)
A convenient sequence for the preparation of 3-alkylidene-2,3-dihydro-1H-isoindol-1-imine derivatives 6 has been developed. Thus, 2-(1-azidoalkyl)benzonitriles 2, readily accessible from 2- Alkylbenzonitriles, are allowed to react with NaH in DMF at 0 to
Acetonitrile as a cyanating reagent: Cu-catalyzed cyanation of arenes
Zhu, Yamin,Zhao, Mengdi,Lu, Wenkui,Li, Linyi,Shen, Zengming
supporting information, p. 2602 - 2605 (2015/06/16)
A novel approach to the Cu-catalyzed cyanation of simple arenes using acetonitrile as an attractive cyano source has been documented. The C-H functionalization of arenes without directing groups involves a sequential iodination/cyanation to give the desired aromatic nitriles in good yields. A highly efficient Cu/TEMPO system for acetonitrile C-CN bond cleavage has been discovered. TEMPO is used as a cheap oxidant and enables the reaction to be catalytic in copper. Moreover, TEMPOCH2CN 6 has been identified as the active cyanating agent and shows high reactivity for forming the -CN moiety.
Efficient selective synthesis of ethylbenzonitriles
Xie, Guangyong,Zhang, Aiqing
experimental part, p. 375 - 379 (2011/11/13)
Ethylbenzonitriles were synthesized by selective gas-phase ammoxidation of ethylbenzyl chlorides prepared by chloromethylation of ethylbenzene in good yields and almost 100% selectivity at ca. 200 °C for the first time.Copyright Taylor & Francis Group, LLC.
A general and efficient suzuki-miyaura cross-coupling protocol using weak base and no water: The essential mole of acetate
Wang, Bing,Sun, Hui-Xia,Sun, Zhi-Hua
experimental part, p. 3688 - 3692 (2009/12/03)
A weak base, CsOAc, promotes Suzuki-Miyaura cross-coupling and related Pd-catalyzed reactions under anhydrous conditions as effectively as stronger bases. Aryl triflates exhibit unusual reaction rates, which are comparable to that: of bromoarenes. A negle
A convenient procedure for palladium catalyzed cyanation using a unique bidentate phosphorus ligand
Jensen, Rader S.,Gajare, Anil S.,Toyota, Kozo,Yoshifuji, Masaaki,Ozawa, Fumiyuki
, p. 8645 - 8647 (2007/10/03)
A palladium complex bearing 1,2-diphenyl-3,4-diphosphinidenecyclobutene ligand (DPCB) has been used to facilitate the catalytic cyanation of aryl bromides. A series of substituted benzonitriles was prepared in good to high yields by the treatment of the corresponding aryl bromides with Zn(CN) 2 in N-methyl-2-pyrrolidone in the presence of 2-4 mol % catalyst at 100°C for 16 h.
Protoberberins from Reissert Compounds VI [1]. Diastereoselective Synthesis and Relative Configuration of 2-Benzoyl-1-cyano-1-(1-phenylalkyl)-1,2-dihydroisoquinolines
Reimann, Eberhard,Erdle, Wolfgang,Weigl, Claudia,Polborn, Kurt
, p. 313 - 326 (2007/10/03)
The alkylation of Reissert compounds 8 by sec-benzyl bromides 4, 7, and 10 diastereoselectively affords the title compounds 11 and 12. X-Ray structure analysis confirms an opposite configuration of the chiral centers in 11 and 12. The benzyl bromides 4, 7, and 10 are prepared by standard procedures.
FLASH PYROLYSIS OF 4-METHYLENE-1,2,3,-BENZOTRIAZINES
Noyce, S. J.,Randles, K. R.,Storr, R. C.
, p. 941 - 944 (2007/10/02)
Flash vacuum pyrolysis of 3-alkyl-4-methylene-1,2,3-bentzotriazines gives products derived from benzocyclobutane N-alkylimines and to a lesser extent from 2-methylene-benzazetidines.Benzocyclobutane N-phenylimine is formed in high yield by flash pyrolytic elimination of HCl from N-phenyl-2-methyl benzimidoyl chloride.
Photochemical Reactions of Dicyanobenzenes with Aliphatic Amines
Ohashi, Mamoru,Miyake, Kentaro,Tsujimoto, Kazuo
, p. 1683 - 1688 (2007/10/02)
Upon irradiation, p-dicyanobenzene reacted with primary, secondary, and tertiary aliphatic amines to give substitution products in which one of the cyano groups was replaced by the amine at α-CH position or by an alkyl group of the amine. o-Dicyanobenzene reacted similarly, but the meta-isomer did not react under similar conditions.The rates of the fluorescence quenching of p-dicyanobenzene with the amines are close to the diffusion-controlled rate, but are somewhat dependent on the ionization potentials of the amines.When the substitution product was irradiated, the cor responding alkylation product was obtained.The mechanism of these reactions have been investigated by the use of such proton donors as MeOH(MeOD); on the basis of those investigations, new photochemical reactions involving charge-transfer, followed by proton-transfer and then addition-elimination, are proposed, as well as a new type of photo-induced Birch reduction
