66693-10-5Relevant academic research and scientific papers
Synthetic method for one-step C-N construction C-S of C-C(I), (C) and (C)-(C) bonds (by machine translation)
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Paragraph 0045-0047; 0061-0062; 0066, (2019/11/28)
An acid load type catalyst is used under the heating C - C condition C - N, C - S and under the heating condition, the α - protonation of the heavy nitrogen ester is carried out, and the construction of the keys is realized in one step, and the method α -
Direct α-Chalcogenation of Aliphatic Carboxylic Acid Equivalents
Gupta, Aniket,Rahaman, Ajijur,Bhadra, Sukalyan
supporting information, p. 6164 - 6168 (2019/08/20)
A novel approach to α-chalcogenation of aliphatic carboxylic acids has been developed by means of transforming them as the corresponding benzazoles. The catalyst system, consisting of CuI, DMSO, and a base, operates through a unique mechanism t
Copper-Catalyzed Carbenoid Insertion Reactions of α-Diazoesters and α-Diazoketones into Si-H and S-H Bonds
Keipour, Hoda,Jalba, Angela,Delage-Laurin, Léo,Ollevier, Thierry
, p. 3000 - 3010 (2017/03/23)
An efficient copper-catalyzed carbenoid insertion reaction of α-diazo carbonyl compounds into Si-H and S-H bonds was developed. A wide range of α-silylesters and α-thioesters was obtained in high yields (up to 98%) from α-diazoesters using 5 mol% of a simple copper(I) salt as catalyst. Using 0.05 mol% of the same catalyst, α-diazoketones led to α-silylketones in low to good yields (up to 70%).
Divergent Roles of Urea and Phosphoric Acid Derived Catalysts in Reactions of Diazo Compounds
Bernardim, Barbara,Couch, Erica D.,Hardman-Baldwin, Andrea M.,Burtoloso, Antonio C. B.,Mattson, Anita E.
, p. 677 - 686 (2016/02/27)
Hydrogen-bond-donor catalysts enable a variety of formal insertion reactions of diazo compounds. The role of the catalyst in the reaction system may vary depending on several factors, including the nucleophilicity of the diazo compound and the acidity of the insertion partner. Ureas and phosphoric acid derivatives can offer complementary reactivity patterns when selected as catalysts for selected O-H and S-H insertion reactions of aryl- and diazo-substituted esters.
Urea-induced acid amplification: A new approach for metal-free insertion chemistry
Couch, Erica D.,Auvil, Tyler J.,Mattson, Anita E.
supporting information, p. 8283 - 8287 (2014/07/08)
The enhanced catalytic activity of difluoroboronate ureas proved to be essential as an acidity amplifier to promote metal-free O-H and S-H insertion reactions of α-aryldiazoacetates in high yield. This methodology was found to be generally applicable to a
Silver-catalysed Doyle-Kirmse reaction of allyl and propargyl sulfides
Davies, Paul W.,Albrecht, Sébastien J.-C.,Assanelli, Giulio
supporting information; experimental part, p. 1276 - 1279 (2009/10/23)
The silver-catalysed Doyle-Kirmse reaction of propargyl and allyl sulfides with diazo compounds is disclosed. The carbon-carbon bond forming process proceeds with a range of substituents and functionality under mild conditions.
PTC sulfanylation of arylacetates
Marzorati, Liliana,Da Silva, Marco Antonio,Wladislaw, Blanka,Di Vitta, Claudio
, p. 3491 - 3495 (2007/10/03)
Phase-transfer catalysis, in the absence of solvent, was successfully applied to the sulfanylation of a series of arylacetates leading, in most cases, to acceptable yields of α-monosulfanylated derivatives.
Synthesis of 4-oxo-2-azetidineacetic acids by means of radical cyclization of N-vinylic α-bromo amides
Ishibashi, Hiroyuki,Kodama, Kazuya,Kameoka, Chisato,Kawanami, Hirotaka,Ikeda, Masazumi
, p. 13867 - 13880 (2007/10/03)
Bu2SnH-mediated radical cyclization of α-bromo amide 8, bearing phenyl and phenylthio substituents at the terminus of the N-vinylic bond, proceeded in a 4-exo-trig manner to give β-lactam 9. Ruthenium tetroxide oxidation of the phenyl group incorporated into the product 9 provided a new synthesis of 4-oxo-2-azetidineacetic acid 13, a useful intermediate for (±)-PS-5. Chiral 4-oxo-2-azetidineacetic acids 23 and 36, key intermediates for the synthesis of (+)-PS-5 and (+)-thienamycin, respectively, were also obtained through the asymmetric radical cyclization of N-vinylic α-bromo amides having chiral auxillaries at the side-chain.
A facile one-pot synthesis of α-hydroxy acids and their derivatives
Florac,Le Grel,Baudy-Floc'h,Robert
, p. 741 - 743 (2007/10/02)
2-Substituted oxirane-1,1-dicarbonitriles react with water, alcohols or phenol to give 2-substituted 2-hydroxyacetic acids, alkyl-2-alkoxyacetates and phenyl 2-phenoxyacetates, respectively. Reaction of 2-substituted oxirane-1,1-dicarbonitrile with thiophenol and a nucleophile, typically water ethanol or urea, gave 2-(phenylthio)acetic acids, ethyl 2-(phenylthio)acetates and N-aminocarbonyl-2-(phenylthio)acetamides.
Thermal and Photochemical Reactions of Organocobaloximes with Diphenyl Disulphide and Diphenyl Diselenide
Deniau, Jean,Duong, Kiem N. V.,Gaudemer, Alain,Bougeard, Peter,Johnson, Michael D.
, p. 393 - 398 (2007/10/02)
Alkyl- and benzyl-bis(dimethylglyoximato)pyridinecobalt(III) complexes react with diphenyl disulphide or diphenyl diselenide, thermally and photochemically, to give good yields of alkyl or benzyl phenyl sulphides or selenides.Chiral alkylcobalt(III) complexes react to give racemic alkyl phenyl sulphides or selenides.Allyl- and propadienyl-bis(dimethylglyoxymato)pyridinecobalt(III) complexes react similarly to give the thermodynamically more stable allyl, propadienyl, or propynyl phenyl sulphides or selenides.These reactions are interpreted in terms of free radical processes in which organic radicals formed as a result of thermal, photochemical, or chemically induced homolysis of the organocobalt complex, attack the diphenyl dichalcogenide to give the product organo phenyl chalcogenide.No evidence could be obtained for the direct attack of phenylthiyl or phenylselenyl radicals on the organic ligand of the organocobalt complexes, though this process cannot be excluded in the case of allylcobalt complexes.
