- Site-Selective C?H Oxygenation via Aryl Sulfonium Salts
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Herein, we report a two-step process forming arene C?O bonds in excellent site-selectivity at a late-stage. The C?O bond formation is achieved by selective introduction of a thianthrenium group, which is then converted into C?O bonds using photoredox chemistry. Electron-rich, -poor and -neutral arenes as well as complex drug-like small molecules are successfully transformed into both phenols and various ethers. The sequence differs conceptually from all previous arene oxygenation reactions in that oxygen functionality can be incorporated into complex small molecules at a late stage site-selectively, which has not been shown via aryl halides.
- Sang, Ruocheng,Korkis, Stamatis E.,Su, Wanqi,Ye, Fei,Engl, Pascal S.,Berger, Florian,Ritter, Tobias
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supporting information
p. 16161 - 16166
(2019/11/03)
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- Efficient recyclable CuI-nanoparticle-catalyzed S-arylation of thiols with aryl halides on water under mild conditions
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CuI nanoparticles efficiently catalyzed the C-S cross coupling of aryl and alkyl thiols with aryl halides in the absence of ligands on water under mild conditions. A wide range of diaryl sulfides and aryl alkyl sulfides are synthesized in good to excellent yields utilizing this protocol. This procedure is particularly noteworthy given its mild conditions, avoiding the undesired formation of disulfides through oxidation of thiols. The recovery and successful reutilization of the catalyst is described. Furthermore, the directed synthesis of bisarylated product is presented. The Royal Society of Chemistry 2012.
- Xu, Hua-Jian,Liang, Yu-Feng,Zhou, Xin-Feng,Feng, Yi-Si
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supporting information; experimental part
p. 2562 - 2568
(2012/04/23)
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- NONCONVENTIONAL FRIEDEL-CRAFTS CHEMISTRY III. ON THE REGIOSPECIFIC SYNTHESIS OF SPIRO-4'-ONE DERIVATIVES
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The rection of 1-oxa-4-thiaspirononan-2-one (4) and/or 1-oxa-4-thiaspirodecan-2-one (5) with arenes (6) under the catalytic action of aluminum chloride afforded in all cases spiro-4'-ones (7a - g and 8a - g), -acetic acid, (9a - g and 10a - g), cycloalkylthioacetic acids, (11 and 20) aryl cycloalkyl sulfides, (14 and 23) diarylsulfides (15), diaryl disulfides and dicycloalkyl disulfides (13 and 22).The mechanisms of these reactions are discussed.Key words: Spiroisothiochroman-4-ones; Friedel-Crafts reactions.
- El-Zohry, Maher F.
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p. 311 - 320
(2007/10/02)
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