- Nickel-catalyzed carbonylation of thioacetates with aryl iodides via CO insertion and C–S bond cleavage
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Aryl thioesters are synthesized via nickel-catalyzed carbonylation of thioacetates with aryl iodides. Alkyl thioacetates undergo coupling with carbon monoxide and aryl iodides to produce the desired aryl thioesters in moderate yields. This catalytic carbonylative coupling process provides a cost-effective and direct approach for the preparation of useful thioesters.
- Lu, Kui,Lv, Ming-Xiu,Mai, Wen-Peng,Sui, Hong-Da
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p. 890 - 895
(2021/07/02)
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- Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light
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A metal- and oxidant-free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10-phenanthrenequinone-promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative power of the method was demonstrated by broad substrate scope and wide functional group tolerance, and enabled the late-stage modification of complex structures, which are difficult to achieve with the existing protocols.
- Zhang, Yueteng,Ji, Peng,Hu, Wenbo,Wei, Yongyi,Huang, He,Wang, Wei
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supporting information
p. 8225 - 8228
(2019/07/16)
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- Rhodium-Catalyzed Decarbonylative Borylation of Aromatic Thioesters for Facile Diversification of Aromatic Carboxylic Acids
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Transformation of aromatic thioesters into arylboronic esters was achieved efficiently using a rhodium catalyst. The broad functional-group tolerance and mild conditions of the method have allowed for the two-step decarboxylative borylation of a wide range of aromatic carboxylic acids, including commercially available drugs.
- Ochiai, Hidenori,Uetake, Yuta,Niwa, Takashi,Hosoya, Takamitsu
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supporting information
p. 2482 - 2486
(2017/02/23)
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- Synthesis of thioesters by simultaneous activation of carboxylic acids and alcohols using PPh3/NBS with benzyltriethylammonium tetrathiomolybdate as the sulfur transfer reagent
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A new and simple route for the synthesis of thioesters starting from carboxylic acids and alcohols is reported by using tetrathiomolybdate as the key sulfur transfer reagent, Triphenylphosphane and N-bromosuccinimide were used for the activation of the ca
- Gopinath, Purushothaman,Vidyarini, Ravindran Sasitha,Chandrasekaran, Srinivasan
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experimental part
p. 6043 - 6047
(2010/03/25)
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- Convenient and efficient synthesis of thiol esters using zinc oxide as a heterogeneous and eco-friendly catalyst
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A catalytic method was developed to synthesize thiol esters from the reaction of acyl chlorides and thiols using zinc oxide as a catalyst under solvent-free conditions at room temperature. Mild reaction conditions, short reaction time, excellent yields of products and recyclability of the catalyst are noteworthy features of this methodology. CSIRO 2008.
- Bandgar, Babasaheb Pandurang,More, Parmeshwar Eknath,Kamble, Vinod Tribhuvannathji,Sawant, Sanjay Suresh
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experimental part
p. 1006 - 1010
(2009/04/05)
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- Zinc promoted convenient and general synthesis of thiol esters
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Synthesis of thiol esters from acyl chlorides and thiols in the presence of activated zinc is described. The recovery of zinc and its reuse makes the procedure more economic.
- Meshram,Reddy, Gondi Sudershan,Bindu, K. Hima,Yadav
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p. 877 - 878
(2007/10/03)
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- THIOL ESTER IN ORGANIC SYNTHESIS XV. REDUCTION WITH TETRABUTYLAMMONIUM BOROHYDRIDE
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Treatment of thiol ester with tetrabutylammmonium borohydride in refluxing chloroform gave rise to the corresponding alcohols.
- Liu, Hsing-Jang,Luo, Weide
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p. 387 - 392
(2007/10/02)
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- Aromatic Substitution. 46. Methyl (Ethyl) Thio(Dithio)carboxylation of Aromatics with S-Methyl (S-Ethyl) Thiocarboxonium and Dithiocarboxonium Fluoroantimonates
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S-Methyl(S-ethyl)thio(dithio)carboxinium ions were prepared by reacting methyl(ethyl) fluoride-antimony pentafluoride with carbonyl sulfide (carbon disulfide) and studied with 1H and 13C NMR spectroscopy.The ions were subsequently used in the novel carboxylation reaction of arenes to S-methyl (S-ethyl) thio(dithio)benzoates.The method was also found to be adaptable to the carboxylation of polystyrene to poly(styrenecarboxylic acid) without degradation of the polymer backbone.
- Olah, George A.,Bruce, Mark R.,Clouet, Francoise L.
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p. 438 - 442
(2007/10/02)
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