1264712-17-5Relevant articles and documents
Transition-Metal-Free Aryl–Aryl Cross-Coupling: C?H Arylation of 2-Naphthols with Diaryliodonium Salts
Ghosh, Manoj K.,Rzymkowski, Jan,Kalek, Marcin
supporting information, p. 9619 - 9623 (2019/07/09)
Transition-metal-free regioselecitive C?H arylation of 2-naphthols with diaryliodonium salts has been developed. The reaction proceeds under very simple experimental conditions and affords a range of products with various substitution patterns. The method allows for the incorporation of electron-deficient aryls, which complements well currently existing metal-free aryl–aryl cross-couplings of phenols that have been so far restricted to the introduction of electron-rich aryl moieties. The mechanism of the reaction was studied by means of DFT calculations, demonstrating that the C?C bond formation occurs via a dearomatization of 2-naphthol substrate, followed by a subsequent rearomatization by tautomerization. The computations show that the use of a low polarity solvent and an insoluble inorganic base is key to securing the high selectivity of the C?C coupling over a competing C?O arylation pathway, by preventing the incipient deprotonation of 2-naphthol.
Organoboron Compound and Method for Manufacturing the Same
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Page/Page column 17, (2012/07/13)
To provide a novel organoboron compound which is useful as a reactant of organic synthesis. To provide a method for manufacturing the organoboron compound. A novel organoboron compound represented by General Formula (G1) below is provided. Note that in General Formula (G1), R1 to R9 separately represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and an aryl group having 6 to 16 carbon atoms. R10 and R11 separately represent hydrogen or an alkyl group having 1 to 6 carbon atoms, and R10 and R11 may be bonded with each other to form a ring. Further, X represents an oxygen atom or a sulfur atom.
Synthesis of functionalized dibenzothiophenes- An efficient three-step approach based on Pd-catalyzed C-C and C-S bond formations
Jepsen, Tue Heesgaard,Larsen, Mogens,Jorgensen, Morten,Solanko, Katarzyna A.,Bond, Andrew D.,Kadziola, Anders,Nielsen, Mogens Brondsted
, p. 53 - 57 (2011/03/21)
A novel and efficient three-step protocol for synthesizing functionalized dibenzothiophenes (DBTs) from common starting materials and by using palladium-catalyzed carbon-carbon and carbon-sulfur bond formations is presented. The reaction conditions offer significantly improved functional-group tolerance and regioselectivity as compared to previously reported methods. A flexible and concise three-step protocol for the synthesis of functionalized dibenzothiophenes DBTs from readily available starting materials is presented. The method is based on two palladium-catalyzed reactions to prepare the masked thiophenols 4followed by deprotection and in situ cyclization to form the DBT skeleton. This approach offers improved functional-group tolerance as well as regiocontrol in the synthesis of functionalized DBTs as compared to previously reported methods.