- Electrochemical C?H Functionalization of (Hetero)Arenes—Optimized by DoE
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A novel approach towards the activation of different arenes and purines including caffeine and theophylline is presented. The simple, safe and scalable electrochemical synthesis of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) aryl ethers was conducted using an easy electrolysis setup with boron-doped diamond (BDD) electrodes. Good yields up to 59 percent were achieved. Triethylamine was used as a base as it forms a highly conductive media with HFIP, making additional supporting electrolytes superfluous. The synthesis was optimized using Design of Experiment (DoE) techniques giving a detailed insight to the significance of the reaction parameters. The mechanism was investigated by cyclic voltammetry (CV). Subsequent transition metal-catalyzed as well as metal-free functionalization led to interesting motifs in excellent yields up to 94 percent.
- D?rr, Maurice,R?ckl, Johannes L.,Rein, Jonas,Schollmeyer, Dieter,Waldvogel, Siegfried R.
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supporting information
p. 10195 - 10198
(2020/07/04)
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- Copper-catalyzed cyanation of heterocycle carbon-hydrogen bonds
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A method for regioselective cyanation of heterocycles has been developed. A number of aromatic heterocycles as well as azulene can be cyanated in reasonable to good yields by using a copper cyanide catalyst and an iodine oxidant.
- Do, Hien-Quang,Daugulis, Olafs
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supporting information; experimental part
p. 2517 - 2519
(2010/08/07)
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- Synthesis of purinecarbonitriles by Pd(0)-catalysed coupling of halopurines with zinc cyanide
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Pd(0)-catalysed coupling of halopurines with zinc cyanide allows the smooth introduction of the cyano group into the purine 2-, 6- and 8-positions. Pronounced ligand effects were observed, and tetrakis(tri-2-furylphosphine)palladium(0) was found to be the
- Gundersen, Lise-Lotte
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- Functionalization including fluorination of nitrogen-containing compounds using electrochemical oxidation
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Nitrogen-containing compounds have been subjected to electrochemical oxidation with Et3N-3HF as an electrolyte. Caffeine afforded 8- fluorocaffeine as a sole product in 40.3% yield. Guanosine tetraacetate and uridine triacetate gave the fluorinated compounds in 17.5 and 4.6% yields, respectively. Similar electrochemical oxidation of caffeine with methanol, KCl, or KCN afforded 8-methoxycaffeine, 8-chlorocaffeine, or 8- cyanocaffeine, respectively.
- Sono, Masakazu,Toyoda, Naoko,Shimizu, Kahori,Noda, Eiji,Shizuri, Yoshikazu,Tori, Motoo
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p. 1141 - 1145
(2007/10/03)
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- Functionalization Including Fluorination of Caffeine, Guanosine Tetraacetate, and Uridine Triacetate using Electrochemical Oxidation
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The title compounds have been subjected to electrochemical oxidation with Et3N-3HF as an electrolyte.Caffeine afforded 8-fluorocaffeine as a sole product in 43percent yield.Guanosine tetraacetate and uridine triacetate gave the fluorinated compounds in 7.3 and 4.8 percent yield, respectively.Similar electrochemical oxidation of caffeine with methanol, KCl or KCN yielded 8-methoxycaffeine, 8-chlorocaffeine, or 8-cyanocaffeine, respecticvely.
- Sono, Masakazu,Toyoda, Naoko,Shizuri, Yoshikazu,Tori, Motoo
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p. 9237 - 9238
(2007/10/02)
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- SOME NEW HALO- AND CYANO-DEMERCURATION REACTIONS OF 8-ACETOXYMERCURI- AND 8,8'-MERCURIBIS-CAFFEINES
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On acting upon 8-acetoxymercuri-caffeine (1) and/or 8,8'-mercuribis-caffeine (2) with aqueous solutions of KI3, KBr3, ICN, BrCN or with an excess of neat liquid SO2Cl2, SCl2, S2Cl2, and SF4, the following 8-X-substituted caffeines, X=CN (3), I (4), Br (5), Cl (6), and F (7), were prepared, sometimes in excellent yields.Seven of these methods of demercuration of organomercurials have not been reported so far in the literature.
- Skulski, Lech,Wroczynski, Piotr
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p. 975 - 982
(2007/10/02)
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