35524-46-0Relevant academic research and scientific papers
DIBENZOTHIOPHENE SALT AS ALKYNYLATING AND CYANATING AGENT
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Paragraph 0098, (2021/08/27)
The present invention describes a new alkynylation and cyanation agent, as well as its preparation and use to introduce nitrile (cyano) or alkyne groups into chemical target molecules by means of an electrophilic reaction. To enable an electrophilic reaction, the chemical backbone of dibenzothiophene was used.
Site-Selective Electrochemical C-H Cyanation of Indoles
Li, Laiqiang,Hou, Zhong-Wei,Li, Pinhua,Wang, Lei
supporting information, p. 5983 - 5987 (2021/08/16)
An electrochemical approach for the site-selective C-H cyanation of indoles employing readily available TMSCN as cyano source has been developed. The electrosynthesis relies on the tris(4-bromophenyl)amine as a redox catalyst, which achieves better yield and regioselectivity. A variety of C2- and C3-cyanated indoles were obtained in satisfactory yields. The reactions are conducted in a simple undivided cell at room temperature and obviate the need for transition-metal reagent and chemical oxidant.
5-(Cyano)dibenzothiophenium Triflate: A Sulfur-Based Reagent for Electrophilic Cyanation and Cyanocyclizations
Li, Xiangdong,Golz, Christopher,Alcarazo, Manuel
supporting information, p. 9496 - 9500 (2019/06/27)
The synthesis of 5-(cyano)dibenzothiophenium triflate 9, prepared by activation of dibenzo[b,d]thiophene-5-oxide with Tf2O and subsequent reaction with TMSCN is reported, and its reactivity as electrophilic cyanation reagent evaluated. The scalable preparation, easy handling and broad substrate scope of the electrophilic cyanation promoted by 9, which includes amines, thiols, silyl enol ethers, alkenes, electron rich (hetero)arenes and polyaromatic hydrocarbons, illustrate the synthetic potential of this reagent. Importantly, Lewis acid activation of the reagent is not required for the transfer process. We additionally report herein biomimetic cyanocyclization cascade reactions, which are not promoted by typical electrophilic cyanation reagents, demonstrating the superior ability of 9 to trigger challenging transformations.
GaCl3-Catalyzed C-H Cyanation of Indoles with N-Cyanosuccinimide
Wang, Xue,Makha, Mohamed,Chen, Shu-Wei,Zheng, Huaiji,Li, Yuehui
, p. 6199 - 6206 (2019/05/24)
An efficient GaCl3-catalyzed direct cyanation of indoles and pyrroles using bench-stable electrophilic cyanating agent N-cyanosuccinimide was achieved and afforded 3-cyanoindoles and 2-cyanopyrroles in good yields and excellent regioselectivities. Notably, this protocol exhibited high reactivity for unprotected indoles and was applicable to a broad range of indole and pyrrole substrates.
Practical synthesis of aromatic nitriles via gallium-catalysed electrophilic cyanation of aromatic C-H bonds
Okamoto, Kazuhiro,Watanabe, Masahito,Murai, Masahito,Hatano, Ryo,Ohe, Kouichi
supporting information; experimental part, p. 3127 - 3129 (2012/04/23)
A gallium-catalysed, direct cyanation reaction of aromatic and heteroaromatic C-H bonds with cyanogen bromide was developed as a practical synthetic method for the preparation of aromatic nitriles. The Royal Society of Chemistry 2012.
Lewis acid catalyzed direct cyanation of indoles and pyrroles with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS)
Yang, Yang,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 5608 - 5611 (2011/12/03)
BF3?OEt2-catalyzed direct cyanation of indoles and pyrroles using a less toxic, bench-stable, and easily handled electrophilic cyanating agent N-cyano-N-phenyl-para-toluenesulfonamide (NCTS) affords 3-cyanoindoles and 2-cyanopyrroles in good yields with excellent regioselectivity. The substrate scope is broad with respect to indoles and pyrroles.
Anodic cyanation of 1-arylpyrroles
Liu, Wei,Ma, Yuan,Yin, Ying-Wu,Zhao, Yu-Fen
, p. 681 - 684 (2007/10/03)
The electrooxidation of several 1-arylpyrroles has been carried out in methanol containing sodium cyanide at a platinum anode in a divided cell. In all instances, replacement of a heteroaromatic hydrogen by a cyano group occurred. On the basis of electroa
Isocyanatophosphoric acid dichloride: A novel reagent for the introduction of a cyano group into the molecules of electron-rich heterocycles and enamines
Smaliy, Radomir V.,Chaikovskaya, Aleksandra A.,Pinchuk, Aleksandr M.,Tolmachev, Andrei A.
, p. 2416 - 2420 (2007/10/03)
A new synthetic method is developed which enables a direct one-step introduction of a cyano group into electron-rich heterocyclic systems of the indole, pyrrole, and indolizine series, and also to enamines using isocyanatophosphoryl dichloride.
