65662-88-6Relevant academic research and scientific papers
Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C?S/C?N Couplings
Martín, M. Trinidad,Marín, Mario,Maya, Celia,Prieto, Auxiliadora,Nicasio, M. Carmen
supporting information, p. 12320 - 12326 (2021/08/09)
Ni-catalyzed C?S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C?O electrophiles in this context is almost uncharted. Here, we describe that preformed Ni(II) precatalysts of the type NiCl(allyl)(PMe2Ar’) (Ar’=terphenyl group) efficiently couple a wide range of (hetero)aryl halides, including challenging aryl chlorides, with a variety of aromatic and aliphatic thiols. Aryl and alkenyl tosylates are also well tolerated, demonstrating, for the first time, to be competent electrophilic partners in Ni-catalyzed C?S bond formation. The chemoselective functionalization of the C?I bond in the presence of a C?Cl bond allows for designing site-selective tandem C?S/C?N couplings. The formation of the two C-heteroatom bonds takes place in a single operation and represents a rare example of dual electrophile/nucleophile chemoselective process.
Spiroconjugated Tetraaminospirenes as Donors in Color-Tunable Charge-Transfer Emitters with Donor-Acceptor Structure
Adachi, Chihaya,Adler, Florin,Chan, Chin-Yiu,Esser, Birgit,Grenz, David C.,Hermann, Mathias,Rose, Daniel,W?ssner, Jan S.,Wilbuer, Jennifer
supporting information, (2021/12/22)
Charge-transfer emitters are attractive due to their color tunability and potentially high photoluminescence quantum yields (PLQYs). We herein present tetraaminospirenes as donor moieties, which, in combination with a variety of acceptors, furnished 12 charge-transfer emitters with a range of emission colors and PLQYs of up to 99 %. The spatial separation of their frontier molecular orbitals was obtained through careful structural design, and two DA structures were confirmed by X-ray crystallography. A range of photophysical measurements supported by DFT calculations shed light on the optoelectronic properties of this new family of spiro-NN-donor-acceptor dyes.
N-bromosuccinimide/HCl mediated reduction of sulfoxides to sulfides
Wang, Jianqiang,Shi, Fangmin,Dai, Dongyan,Xiong, Liping,Yang, Yongpo
supporting information, p. 439 - 443 (2021/02/03)
An efficient reduction of sulfoxides to sulfides mediated by N-bromosuccinimide (NBS)/HCl system has been developed. This protocol shows good functional group compatibility as well as broad substrates scope with operational simplicity.
Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds
Lam, Long Yin,Ma, Cong
supporting information, p. 6164 - 6168 (2021/08/16)
A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.
Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters
Cao, Han,Liu, Xuejing,Bie, Fusheng,Shi, Yijun,Han, Ying,Yan, Peng,Szostak, Michal,Liu, Chengwei
, p. 10829 - 10837 (2021/07/28)
Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.
X-ray structurally characterized Mo (VI), Fe (III) and Cu (II) complexes of amide-imine conjugate: (bio)catalytic and histidine recognition studies
Ta, Sabyasachi,Ghosh, Milan,Salam, Noor,Das, Jayanta,Islam, Manirul,Brand?o, Paula,Félix, Vítor,Sanmartin, Jesus,Das, Debasis
, (2020/07/13)
An amide-imine conjugate, (E)-N′-((2-hydroxybenzen-1-yl) methylene)-4-methylbenzohydrazide (H2LPTASAL), derived from 4-methyl-benzoic acid hydrazide (PTA) and 2-hydroxybenzaldehyde is used to prepare Mo (VI), Cu (II) and Fe (III) complexes. The X-ray structurally characterized complexes have been explored as catalyst for amine assisted asymmetric ring opening (ARO) of epoxide, carbon-heteroatom cross-coupling and ethyl benzene oxidation. In addition, their catecholase like activities have thoroughly been investigated. Moreover, the Cu (II) complex selectively recognizes histidine by fluorescence spectroscopy.
Preparation method of 4-phenylmercaptothiophenol
-
Paragraph 0056-0059; 0067; 0068, (2020/07/15)
The invention provides a preparation method of 4-phenylthiolthiophenol. The preparation method comprises the following steps: performing a bromination reaction on diphenyl sulfide and a bromination reagent to prepare 4-bromodiphenyl sulfide, performing a
An effective thermally activated delayed fluorescence host material for highly efficient blue phosphorescent organic light-emitting diodes with low doping concentration
Liu, Yan,Pan, Jie,Chen, Feng,Gao, Kun,Zhu, Aiyun,Wang, Ruoxian,Yue, Xuan,Ban, Xinxin
, (2019/11/28)
A thermally activated delayed fluorescence (TADF) material BCz-2SO has been designed and synthesized as host for blue phosphorescent organic light-emitting diodes (OLEDs). Photophysical studies and theoretical calculations show that the molecule has a small singlet-triplet energy gap (ΔEST) of 0.345 eV, which is beneficial to the reverse energy transferring between the singlet and triplet state. Thanks to the TADF property, the triplet energy can be transmitted to the singlet state through reverse intersystem crossing (RISC), and then transmitted to the guest through the Fo?rster energy transfer (FET) to achieve 100% utilization of energy. Thus, the triplet–triplet annihilation (TTA) of the blue phosphor can be avoided by the extremely low doping concentration of 1%. By using BCz-2SO as the host of FIrpic, the solution-processed blue phosphorescent device achieves the maximum current efficiency (CE), power efficiency (PE), external quantum efficiency (EQE) and highest brightness of 16.38 cd A?1, 9.04 lm W?1, 7.8% and 16,537 cd m-2, respectively. It demonstrates that one can employ the solution-processed method to prepare the high performance phosphorescent OLEDs using the TADF host material we have developed.
Microwave-Assisted Copper Slag-Catalyzed Green S-Arylation of Arenethiols with Arylboronic Acids
Gavane, D. S.,Jambhorkar, V. S.,Kale, B. D.,Karnik, K. S.,Khandare, A. L.,Narula, I. S.,Rajhans, A. P.,Sarkate, A. P.
, p. 1300 - 1303 (2020/10/02)
Abstract: Diaryl sulfides have been synthesized in moderate to excellent yield by S-arylation of arenethiols with arylboronic acids using copper slag as a catalyst. Copper slag is a by-product obtained from smelting and refining of copper. Conventional heating method has been compared with the microwave-assisted technique. The proposed microwave-assisted synthesis provides excellent yields of diaryl sulfides in a short time (10 min) and is ligand-free, green, and cost-effective.
Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: Synthesis of diarylsulfides
Bhowmik, Amit,Fernandes, Rodney A.,Yadav, Mahesh
, p. 2447 - 2458 (2020/04/15)
A NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air. This methodology is reliable and offers a mild and easy to operate process for the synthesis of arylthioethers, which are essential compounds with applications in the pharmaceutical and agricultural industries. This method avoids the use of expensive transition metals, such as Pd, Ir or Rh, sophisticated ligands and elevated temperatures. It also has a wide substrate scope (55 examples) and provides products in good to excellent yields (72-93%).
