31317-07-4Relevant academic research and scientific papers
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.).
Cyclization of 2-Biphenylthiols to Dibenzothiophenes under PdCl2/DMSO Catalysis
Zhang, Tao,Deng, Guigang,Li, Hanjie,Liu, Bingxin,Tan, Qitao,Xu, Bin
, p. 5439 - 5443 (2018/09/13)
A palladium-catalyzed synthesis of dibenzothiophenes from 2-biphenylthiols is described. This highly efficient reaction employs a simple PdCl2/DMSO catalytic system, in which PdCl2 is the sole metal catalyst and DMSO functions as an oxidant and solvent. This transformation has broad substrate scope and operational simplicity and proceeds in high yield. The synthetic utility was demonstrated by the facile synthesis of helical dinapthothiophene 3 and an eminent organic semiconductor DBTDT 4. Importantly, highly strained trithiasumanene 5, a buckybowl of considerable synthetic challenge, was observed under this catalytic system.
Palladium catalysis based one-pot synthesis method for DBTs (dibenzothiophenes)
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Paragraph 0033-0038, (2020/05/12)
The invention discloses a palladium catalysis based one-pot synthesis method for DBTs (dibenzothiophenes). An inorganic base is added to an N,N-dimethylacetamide solution, with a palladium catalyst/ligand as a catalysis system, o-bromoiodobenzene derivatives or iodobenzene derivatives and thiophenol derivatives taken as raw materials are subjected to a reaction in nitrogen atmosphere, and DBTs areobtained through separation. The simple, economical and easily available raw materials are taken as substrates, all-position-substituted DBTs are synthesized on the basis of palladium catalyzed cascade reaction, and DBTs have great application prospect in medical synthesis intermediates and organic optoelectronic material science.
A Pd-catalyzed optional approach for the synthesis of dibenzothiophenes
Song, Juan,Wu, Hao,Sun, Wei,Wang, Songjiang,Sun, Haisen,Xiao, Kang,Qian, Yan,Liu, Chao
supporting information, p. 2083 - 2087 (2018/03/26)
A direct and practical approach for the construction of DBTs was developed via a Pd-catalyzed tandem reaction, in which commercially available o-bromo-iodobenzenes combined with benzene thiols or iodobenzenes combined with o-bromo-benzene thiols were applied. These two approaches will provide an alternative for the synthesis of DBT derivatives.
Green Preparation of Dibenzothiophene Derivatives Using 2-Biphenylyl Disulfides in the Presence of Molecular Iodine and Its Application to Dibenzoselenophene Synthesis
Nishino, Kota,Ogiwara, Yohei,Sakai, Norio
supporting information, p. 5892 - 5895 (2017/10/31)
A protocol for the direct preparation of dibenzothiophenes from 2-biarylyl disulfides in the presence of an economic and ecological oxidant, molecular iodine, was explored. This protocol was used for the direct preparation of dibenzoselenophene.
Diaryl ring fused sulfides and diaryl ring fused selenides, and synthesis method and application thereof
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Paragraph 0069; 0070; 0071; 0072, (2017/06/20)
The invention discloses a synthesis method of diaryl ring fused sulfides represented by formula (B) and diaryl ring fused selenides represented by formula (C). The method is characterized in that a reaction of a reaction raw material high-iodine salt is carried out in dimethyl sulfoxide under the action of an inorganic sulfuration reagent or selenylation reagent and an alkali at 60-100 DEG C to obtain the diaryl ring fused sulfides and the diaryl ring fused selenides. Sulfur or selenium is introduced in the later stage in the presence of a nonmetal catalyst, so poisoning of sulfur to a metal catalyst in the early stage reaction is avoided; the above inorganic sulfur source is nontoxic and odorless; and two aryl groups in the high-iodine salt are fully used, so the atom economy and the greenness of the method are fully shown. The diaryl ring fused sulfides and the diaryl ring fused selenides prepared through the method can be applied to synthesize photoelectric materials BTBT and BTBS.
Transition-Metal-Free Diarylannulated Sulfide and Selenide Construction via Radical/Anion-Mediated Sulfur-Iodine and Selenium-Iodine Exchange
Wang, Ming,Fan, Qiaoling,Jiang, Xuefeng
supporting information, p. 5756 - 5759 (2016/11/17)
A facile, straightforward protocol was established for diarylannulated sulfide and selenide construction through S-I and Se-I exchange without transition metal assistance. Elemental sulfur and selenium served as the chalcogen source. Diarylannulated sulfides were systematically achieved from a five- to eight-membered ring. A trisulfur radical anion was demonstrated as the initiator for this radical process via electron paramagnetic resonance (EPR) study. OFET molecules [1]benzothieno[3,2-b][1]benzothiophene (BTBT) and [1]benzothieno[3,2-b][1]benzoselenophene (BTBS) were efficiently established.
Synthesis of dibenzothiophenes by pd-catalyzed dual C-H activation from diaryl sulfides
Che, Rui,Wu, Zhiqing,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge
supporting information, p. 7258 - 7261 (2014/06/23)
Palladium-catalyzed dual C-H functionalization of diaryl sulfides to form dibenzothiophenes (DBTs) by oxidative dehydrogenative cyclization is reported. This protocol afforded various DBTs in moderate to good yields with tolerance of a wide variety of substrates. Benzo[1,2-b:4,5-b]bis[b]benzothiophene was successfully synthesized by this method, which was used as an organic semiconductor for field-effect transistors.
Efficient synthesis of unsymmetrical dibenzothiophenes by acid-mediated intramolecular cyclization of biaryl methyl sulfoxides
Pandya, Vrajesh B.,Jain, Mukul R.,Chaugule, Balaji V.,Patel, Jigar S.,Parmar, Bhavesh M.,Joshi, Jignesh K.,Patel, Pankaj R.
, p. 497 - 505 (2011/11/29)
Aconvenient and high-yielding synthesis of unsymmetrical dibenzothiophenes has been achieved by an acid-mediated ring closure of the biphenyl ring having a sulfoxide substituent at the ortho position. Various functional groups are well tolerated in this methodology. Taylor & Francis Group, LLC.
Palladium-catalyzed double C-H activation directed by sulfoxides in the synthesis of dibenzothiophenes
Samanta, Rajarshi,Antonchick, Andrey P.
, p. 5217 - 5220 (2011/07/08)
S=O shows where to go: A novel double C-H activation of aromatic compounds with a sulfoxide as a directing group results in the highly regioselective synthesis of polysubstituted dibenzothiophenes (see scheme). The reaction cascade consists of palladium-catalyzed double C-H activation and a Pummerer rearrangement followed by palladium-catalyzed C-S bond formation. Copyright
