16939-05-2Relevant articles and documents
Nickel/β-CD-catalyzed Suzuki–Miyaura cross-coupling of aryl boronic acids with aryl halides in water
Payamifar, Sara,Kazemi, Foad,Kaboudin, Babak
, (2021)
In this study, a convenient nickel-catalyzed protocol has been introduced for the Suzuki–Miyaura coupling reaction. A simple mixture of Ni(II) and unfunctionalized β-cyclodextrin (β-CD) was used to cross-coupling of aryl halides with aryl boronic acids for the synthesis of biaryls in water. β-CD is a water-soluble seminatural cyclic oligosaccharide, environmentally friendly biomaterial, inexpensive, and commercially available ligand. This ligand with low solubility in usual organic solvents has been used for the synthesis of biaryls in good to excellent yields. The cross-coupling results in the presence of Ni(II)/β-CD catalytic system showed that the coupling reaction carried out with appropriate yields for both electron-rich and electron-deficient aryl halides. The coupling reaction completed in water as a green solvent. The catalyst was also recycled for four runs with a small decrease in its catalytic activity. The presented new method allows an easier and more cost-efficient synthesis of biaryls from the reaction of arylboronic acids with various aryl halides in water.
Synthesis of 3-aryl thiophenes from disodium 2-aryl succinates: Role of red phosphorus
Marwah,Marwah,Shankar Rao,Trivedi
, p. 235 - 243 (1995)
Role played by red phosphorus in the synthesis of 3-aryl thiophenes from disodium 2-aryl succinates using P4S10 discussed. A new simple method for the synthesis of 2-(4-methylphenyl)succinic acid is also described.
Redox-Divergent Construction of (Dihydro)thiophenes with DMSO
Chen, Qing-An,He, Gu-Cheng,Hu, Yan-Cheng,Ji, Ding-Wei,Liu, Heng,Zhang, Xiang-Xin,Zhao, Chao-Yang
supporting information, p. 24284 - 24291 (2021/10/08)
Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules. Inspired by the redox diversity of these features in nature, we demonstrate herein a redox-divergent construction of dihydrothiophenes, thiophenes, and bromothiophenes from the respective readily available allylic alcohols, dimethyl sulfoxide (DMSO), and HBr. The redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations, including the preparation of bioactive and functional molecules.
Modular and Selective Arylation of Aryl Germanes (C?GeEt3) over C?Bpin, C?SiR3 and Halogens Enabled by Light-Activated Gold Catalysis
Dahiya, Amit,Fricke, Christoph,Funes-Ardoiz, Ignacio,Gevondian, Avetik G.,Schoenebeck, Franziska,Sherborne, Grant J.
, p. 15543 - 15548 (2020/06/22)
Selective C (Formula presented.) –C (Formula presented.) couplings are powerful strategies for the rapid and programmable construction of bi- or multiaryls. To this end, the next frontier of synthetic modularity will likely arise from harnessing the coupling space that is orthogonal to the powerful Pd-catalyzed coupling regime. This report details the realization of this concept and presents the fully selective arylation of aryl germanes (which are inert under Pd0/PdII catalysis) in the presence of the valuable functionalities C?BPin, C?SiMe3, C?I, C?Br, C?Cl, which in turn offer versatile opportunities for diversification. The protocol makes use of visible light activation combined with gold catalysis, which facilitates the selective coupling of C?Ge with aryl diazonium salts. Contrary to previous light-/gold-catalyzed couplings of Ar–N2+, which were specialized in Ar–N2+ scope, we present conditions to efficiently couple electron-rich, electron-poor, heterocyclic and sterically hindered aryl diazonium salts. Our computational data suggest that while electron-poor Ar–N2+ salts are readily activated by gold under blue-light irradiation, there is a competing dissociative deactivation pathway for excited electron-rich Ar–N2+, which requires an alternative photo-redox approach to enable productive couplings.
