22751-52-6Relevant articles and documents
Thermally-stable 2,3-diphenylated benzotiophene containing host materials for red phosphorescent organic light-emitting diodes
Jeon, Joon Ho,Lee, Nam-Jin,Lee, Ji-Hoon,Suh, Min Chul
, p. 116 - 123 (2014)
This study reports a series of benzo[b]thiophene (BT) derivatives with good electronic properties as host materials for red phosphorescent organic light-emitting diodes (PHOLEDs). We applied thermally-stable materials for red PHOLEDs which contain BT and carbazole moieties which also provide a good charge transport ability, as well as a good charge confinement effect (T1 > 2.25 eV). To control the appropriate charge transporting ability, two different structures having one or two carbazole units connected to the single BT moiety were prepared. Using this approach, we found that the material with a single carbazole and a single BT unit showed the best current efficiency and external quantum efficiency (up to 23.6 cd/A and 12.8%, respectively). The results of the experiment also suggest that BT could be used as an electron-transporting unit when utilized with carbazole moiety, although it has previously been utilized as a p-type material.
B(C6F5)3-Catalyzed cyclization of alkynes: direct synthesis of 3-silyl heterocyclic compounds
Li, Mengxing,Wang, Ting,An, Zhenyu,Yan, Rulong
supporting information, p. 11953 - 11956 (2020/10/15)
An efficient one-pot strategy for easy access to 3-silyl heterocyclic compounds was developedviaa B(C6F5)3-catalyzed cycloaddition reaction ofo-(1-alkynyl)(thio)anisoles oro-(1-alkynyl)-N-methylaniline. In this reaction, benzenethiophene, benzofuran or indole skeletons could be constructed by an intermolecular cyclization with diphenylsilane. This protocol elicited moderate-to-good yields with metal-free reaction systems.
Synthesis of Benzo[b]thiophenes through Rhodium-Catalyzed Three-Component Reaction using Elemental Sulfur
Moon, Sanghun,Kato, Moena,Nishii, Yuji,Miura, Masahiro
supporting information, p. 1669 - 1673 (2020/03/23)
A benzo[b]thiophene synthesis by Rh-catalyzed three-component coupling reaction of arylboronic acids, alkynes, and elemental sulfur (S8) is developed. A notable feature of this protocol is that the thienannulation (thiophene annulation) proceeds with high regioselectivity via the sequential alkyne insertion, C?H activation, and then sulfur atom transfer to the metallacycle intermediate. In a similar manner, dibenzothiophenes can be synthesized from the parent biarylboronic acids and S8. (Figure presented.).
Visible-light-induced tandem cyclization of 2-alkynylanilines with disulfides: A convenient method for accessing benzothiophenes under transition-metal-free and photocatalyst-free conditions
Xie, Xiaoyu,Li, Pinhua,Shi, Qing,Wang, Lei
, p. 7678 - 7684 (2017/09/27)
A simple and efficient strategy for the preparation of benzothiophenes via visible-light-induced cyclization of 2-alkynylanilines with disulfides was developed. The reaction afforded the desired products in good yields at room temperature under transition-metal-free and photocatalyst-free conditions.
A practical synthesis of benzothiophenes via visible-light-promoted cyclization of disulfides and alkynes
Ye, Lin-Miao,Qian, Lu,Chen, Yan-Yan,Zhang, Xue-Jing,Yan, Ming
supporting information, p. 550 - 554 (2017/01/25)
Visible-light-promoted intermolecular radical cyclization of disulfides and alkynes has been developed. Benzothiophenes bearing ester, ketone, aldehyde and aryl substituents were synthesized in good yields. The reaction was carried out in the absence of t
AlCl3-Catalyzed Intermolecular Annulation of Thiol Derivatives and Alkynes by 1,2-Sulfur Migration: Construction of 6-Substituted Benzo[b]thiophenes
Ramesh,Guntreddi, Tirumaleswararao,Sahoo, Akhila K.
, p. 4405 - 4413 (2017/08/23)
A method for the AlCl3-catalyzed intermolecular oxidative annulation of N-(arylthio)phthalimide derivatives with alkynes has been developed. The annulation reaction occurs at room temperature and involves the oxidative cleavage of the S–N bond and 1,2-sulfur migration, which leads to the construction of diverse arrays of π-conjugated 6-substituted 2,3-diarylbenzo[b]thiophene derivatives.
Photopromoted Entry to Benzothiophenes, Benzoselenophenes, 3H-Indoles, Isocoumarins, Benzosultams, and (Thio)flavones by Gold-Catalyzed Arylative Heterocyclization of Alkynes
Alcaide, Benito,Almendros, Pedro,Busto, Eduardo,Herrera, Fernando,Lázaro-Milla, Carlos,Luna, Amparo
supporting information, p. 2640 - 2652 (2017/08/16)
Visible light-promoted and gold-photoredox-catalyzed reactions of heteroatom (N, S, Se, O) tethered alkynes with arenediazonium salts selectively proceeded to build vicinal diaryl-substituted 2H-benzo[e][1,2]thiazine 1,1-dioxides (benzosultams), benzoselenophenes, benzothiophenes, 4H-chromen-4-ones (flavones), 3H-indoles, 1H-isochromen-1-ones (isocoumarins), and 4H-thiochromen-4-ones (thioflavones). Moreover, the utility of functionalized 3H-indoles as precursors for further elaboration has been demonstrated with the switchable and facile preparation of 1H-indoles, 2-oxindoles, and 3-oxindolines. (Figure presented.).
Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzothiophenes via the Annulation of Aryl Sulfides with Alkynes
Masuya, Yoshihiro,Tobisu, Mamoru,Chatani, Naoto
supporting information, p. 4312 - 4315 (2016/11/03)
A new method has been developed for the synthesis of 2,3-disubstituted benzothiophenes involving the palladium-catalyzed annulation of aryl sulfides with alkynes. This convergent approach exhibited good functional group tolerance, providing rapid access to a diverse array of derivatives from simple, readily available starting materials. This protocol can also be used to synthesize 2-silyl-substituted benzothiophenes, which can be used as versatile platforms for the synthesis of 2,3-unsymmetrically substituted benzothiophenes.
Pd/phenanthroline-catalyzed arylative cyclization of o-(1-alkynyl)thioanisoles: Synthesis of 3-arylated benzo[b]thiophenes
Yamauchi, Takayuki,Shibahara, Fumitoshi,Murai, Toshiaki
supporting information, p. 2945 - 2948 (2016/07/06)
The arylative cyclization of o-(1-alkynyl)thioanisoles with aryl iodides in the presence of catalytic amounts of [Pd(phen)2][PF6]2resulted in the efficient formation of 3-arylated benzo[b]thiophenes, and a range of aryl iodides with electron-donating or -withdrawing groups could be used. While this reaction proceeded in the presence of aromatic and aliphatic groups on the terminal alkynyl carbon atom, silyl and alkoxycarbonyl groups hampered the reaction. Furthermore, this method could be extended to the synthesis of 3-arylated indoles from N,N-dimethyl-o-(1-alkynyl)aniline. All these reactions proceeded smoothly via cleavage of the carbon-heteroatom bond. In addition to the desired cyclization products, the use of a o-(hydroxypropyl)phenylmethyl substituent on the sulfur atom afforded isochroman, which should be formed by the intramolecular attack of a hydroxy group onto the benzylic carbon atom.
Radical Cyclization of Arenesulfonyl Chlorides and Alkynes: A Rapid Access to π-Conjugated Benzothiophenes
Wan, Danyang,Yang, Yudong,Liu, Xingyan,Li, Mingliang,Zhao, Siling,You, Jingsong
supporting information, p. 55 - 59 (2016/01/20)
A metal-free radical cyclization of arenesulfonyl chlorides with alkynes has been developed, which provides a rapid and practical access to a variety of π-conjugated benzothiophenes with a broad reactive functional group tolerance. Furthermore, dialkynyl compounds could also undergo this transformation to give extended π-systems in good yields.
