- Iodine(III) Enabled Dehydrogenative Aryl C?S Coupling by in situ Generated Sulfenium Ion
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Due to the normal polarity preferences, arenes form stable complexes with thiols through S?H???π interaction and direct dehydrogenative aryl C?S coupling is usually restricted. We report here an umpolung based one pot and direct C?S coupling approach unde
- Choudhuri, Khokan,Maiti, Saikat,Mal, Prasenjit
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p. 1092 - 1101
(2019/01/30)
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- Palladium catalyzed aryl(alkyl)thiolation of unactivated arenes
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A general palladium-catalyzed aryl(alkyl)thiolation of various substituted unactivated arenes is accomplished for the synthesis of diverse unsymmetrical diaryl(alkyl) sulfides in good yield employing electrophilic sulfur reagent 6 derived from succinimide. The developed strategy was coupled with intramolecular arylation of a C-H bond to afford dibenzothiphene derivatives, an important moiety in material science as organic semiconductors.
- Saravanan, Perumal,Anbarasan, Pazhamalai
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supporting information
p. 848 - 851
(2014/03/21)
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- Carbon-sulfur bond formation catalyzed by [Pd(IPr*OMe) (cin)Cl] (cin = cinnamyl)
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The newly prepared complex [Pd(IPr*OMe)(cin)(Cl)] provides high catalytic activity for carbon-sulfur cross-coupling reactions. Nonactivated and deactivated aryl halides were successfully coupled with a large variety of aryl- and alkylthiols using this well-defined palladium N-heterocyclic carbene (NHC) complex.
- Bastug, Gulluzar,Nolan, Steven P.
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supporting information
p. 9303 - 9308
(2013/10/08)
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- Potassium isopropoxide: For sulfination it is the only base you need!
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PEPPSI max: KOiPr has been identified as the key ingredient for Pd-catalyzed sulfination (see scheme). Potassium is essential to keep the thiol concentration low, and isopropoxide is necessary for precatalyst activation and to break up Pd-sufide-based resting states. Together with the reactive Pd-PEPPSI-IPentCl o-picoline catalyst, this system couples profoundly deactivated partners at RT that other catalysts cannot accomplish in refluxing toluene. Copyright
- Sayah, Mahmoud,Organ, Michael G.
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supporting information
p. 16196 - 16199
(2013/12/04)
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- Carbon-sulfur bond formation of challenging substrates at low temperature by using Pd-PEPPSI-IPent
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Aryl thiols made cool and quick: The coupling of alkyl, aryl, and silyl thiols to hindered, deactivated aryl bromides and chlorides has been achieved under the most mild temperatures yet reported (i.e., room temperature to 40°C). The bulk afforded by the di-2,6-(3-propylphenyl)imidazolium-derived Pd-PEPPSI-IPent catalyst is believed to actively promote the critical reductive elimination step of the catalytic cycle, thereby eliminating the formation of poisonous off-cycle dimeric resting states that have plagued Pd-catalyzed sulfination reactions.
- Sayah, Mahmoud,Organ, Michael G.
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supporting information; experimental part
p. 11719 - 11722
(2011/11/29)
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- Facile and efficient sulfenylation method using quinone mono-O,S-acetals under mild conditions
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A novel sulfenylation method induced by aromatization of quinone mono-O,S-acetals is described. These sulfenylation reagents readily react with silyl enolethers or electron rich aromatic compounds to give sulfenylation products under mild conditions. In particular, O,S-acetal 2j, which possesses a pentafluorophenylthio function, is the most effective reagent from the standpoint of the adaptability for various substrates.
- Matsugi,Murata,Gotanda,Nambu,Anilkumar,Matsumoto,Kita
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p. 2434 - 2441
(2007/10/03)
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- A novel efficient sulfenylation method using quinone mono-O,S-acetals under mild conditions
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A novel method for sulfenylation induced by aromatization of quinone mono-O,S-acetals is described.
- Matsugi, Masato,Gotanda, Kentoku,Murata, Kenji,Kita, Yasuyuki
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p. 1387 - 1388
(2007/10/03)
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