Ag(I)-Catalyzed C-H Carboxylation of Thiophene Derivatives
CO2utilization is an attractive aspect as it allows the direct conversion of CO2into valuable chemicals. In this regard, direct incorporation of CO2into the C-H bond of heteroaromatic compounds is important due to the ubiquitous structural motifs of the heteroaromatic carboxylic acids. Herein, we report the Ag-catalyzed C-H carboxylation of thiophene derivatives. This new catalytic system involving a phosphine ligand and lithiumtert-butoxide enables the direct carboxylation of thiophenes under mild reaction conditions. Experimental studies revealed that the use oftert-butyl alkoxide is critical for the exergonic formation of an arylsilver intermediate, and the results were further supported by density functional theory calculations.
Lee, Mijung,Hwang, Young Kyu,Kwak, Jaesung
supporting information
p. 3136 - 3144
(2021/09/30)
β-Selective C?H Arylation of Electron-Deficient Thiophenes, Pyrroles, and Furans
A general β-C?H arylation of electron-deficient thiophenes, pyrroles, and furans has been developed using ligand-modulated palladium catalyst. The use of a modified norbornene is crucial for reversing the conventional α-selectivity of these substrates. This method features good yields, high β-selectivity, and good tolerance of functional groups.
Liu, Luo-Yan,Qiao, Jennifer X.,Ewing, William R.,Yeung, Kap-Sun,Yu, Jin-Quan
p. 416 - 418
(2020/02/20)
In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides
A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is
Milner, Phillip J.,Yang, Yang,Buchwald, Stephen L.
supporting information
p. 4775 - 4780
(2015/10/28)
The application of vinamidinium salts to the synthesis of 2,4-disubstituted thiophenes
The synthesis of 2,4-disubstituted thiophenes by the condensation of symmetrical vinamidinium salts with methyl thioglycolate has been accomplished for the first time. Simple experimental conditions were used to prepare seven different methyl 4-aryl-2-thi
Clemens, Ryan T.,Smith, Stanton Q.
p. 1319 - 1320
(2007/10/03)
3-alkyl or aryl thiophenes from malonaldehyde derivatives
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Kirsch,Prim
p. 1721 - 1726
(2007/10/02)
Fused Heterocycles from Pyrrolethiols.Thienopyrroles,Thienopyroles and THiazolopyrroles from Pyrrol-2-yl Phenacyl Sulfides
A reinvestigation of the cyclization of pyrrol-2-yl phenacyl sulfides in polyphosphoric acid has shown that the major product is a thienopyrrole, where rearrangement of the sulfur substituent from position 2 to position 3 has preceded cyclization.W
Harris, Roger L.N.,McFadden, Helen G.
p. 887 - 892
(2007/10/02)
Synthese d'amino-3 thiophenes a partir d'aryl- et d'hetaryl-acetonitrile (1)
Applying Fiesselman's condensation to α-hydroxymethylene nitriles the authors describe a synthesis of substituted aminothiophenes.
Kirsch, G.,Cagniat, D.,Cagniat, P.
p. 443 - 445
(2007/10/02)
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