- Zinc-catalyzed regioselective addition of alkyl thiols to alkenes via anion or radical reactions
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Zn-catalyzed reactions of alkenes with alkyl thiols could afford alkyl sulfides regioselectively. When the ZnI2- catalyzed hydrothiolation of alkenes was achieved using alkyl thiols at 100 °C, Markovnikov-type alkyl sulfides were obtained in excellent yields without the formation of linear products. To the contrary, Zn(OAc)2- catalyzed reaction gave rise only to anti-Markovnikov-type products regioselectively. The reaction proceeded via a radical process.
- Taniguchi, Nobukazu
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p. 125 - 137
(2021/03/17)
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- Br?nsted Acid-Assisted Zinc-Catalyzed Markovnikov-Type Hydrothiolation of Alkenes Using Thiols
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The zinc-catalyzed regioselective hydrothiolation of alkenes with thiols was achieved in the presence of 4-toluenesulfonic acid. Through this procedure, Markovnikov-type sulfides were synthesized in excellent yields, and the formation of anti-Markovnikov-
- Taniguchi, Nobukazu
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p. 6528 - 6534
(2020/07/14)
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- Highly Efficient and Chemoselective Tertiary and Secondary Benzylation of Thiols Catalyzed by Indium(III) Triflate
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Several examples of nucleophilic substitution reactions of compounds that have good leaving groups have been previously reported, but the direct use of simple alcohols still remains a challenge because of the poor leaving ability of the hydroxy group. Herein, an efficient and highly chemoselective method for the S-benzylation of a wide range of aromatic and aliphatic thiols has been accomplished in the presence of catalytic amounts (0.1–0.2 mol-%) of indium(III) triflate. Our approach is atom efficient (water is the only byproduct) and suitable to obtain the corresponding unsymmetrical thioethers in excellent yields (up to 99 %). The low loading of catalyst that are needed to obtain extraordinarily high chemoselectivities and the generality of the reaction make this approach unique.
- Kuciński, Krzysztof,Hreczycho, Grzegorz
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p. 5572 - 5581
(2017/10/13)
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- One-pot reductive sulfenylation and thiocyanation of carbonyl compounds in ionic liquid media
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The first example of an efficient one-pot reductive sulfenylation and thiocyanation of carbonyl compounds in environmentally benign ionic liquid (IL) media is reported. The process involves reduction of carbonyl compounds with NaBH4 in the IL [bmim]BF4 followed by I2-catalyzed reaction of the resulting alcohols with aromatic/aliphatic thiols or ammonium thiocyanate in the same vessel to afford sulfides or thiocyanates, respectively, in excellent yields (78-93%). Notably, the protocol precludes the necessity to prepare and isolate the intermediate alcohols in a separate step as they are formed in situ, and the IL used can be recycled easily for further use without any loss of efficiency. Copyright
- Yadav, Lal Dhar S.,Garima,Kapoor, Ritu
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p. 100 - 112
(2011/03/17)
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- Palladium-catalyzed SN1 reactions of secondary benzylic alcohols: Etherification, amination, and thioetherification
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The reaction of various secondary benzylic alcohols in the presence of PdII catalysts provides ethers in good to high yields, Unsymmetric ethers could also be obtained with good selectivity by coupling two different alcohols. Direct amination is observed with electron-deficient anilines, and thioethers are prepared conveniently in high yields by the direct action of thiols on sec-phenylethyl alcohol. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Miller, Kimberly J.,Abu-Omar, Mahdi M.
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p. 1294 - 1299
(2007/10/03)
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- Thioketones and Enethiolates by 1,3-Anionic Cycloreversion of Dithiolane Derivatives
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The reactive (ar)aliphatic thioketones 3a-c are generated by cycloreversion of the anions 2 of 1,3-dithiolane-4,5-dicarboxylates 1 and are trapped by mesitonitrile oxide (5) in a 1,3-dipolar cycloaddition to give 7.From the fragmentation of anions 12 of 1,3-dithiolane 1,1-dioxides 11, thiobenzophenone (3d) and thiocamphor (3e) are isolated, wheras thioketones 3a,c with α-hydrogen are deprotonated in situ to provide enethiolates 13.Anions 13 add nitrile oxide 5 to yield thiohydroximates 8.
- Schaumann, Ernst,Ruehter, Gerd
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p. 1159 - 1164
(2007/10/02)
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- Chemistry of Amine-Boranes. Part 10. Synthesis of Sulphides from Dithioacetals using Pyridine-Borane in Acid
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The synthesis of sulphides from dithioacetals in trifluoroacetic acid or in dichloromethane in the presence of aluminium chloride with pyridine-borane is described.
- Kikugawa, Yasuo
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p. 609 - 610
(2007/10/02)
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- A NEW SYNTHESIS OF SULFIDES FROM THIOLS AND ALDEHYDES OR KETONES WITH PYRIDINE-BORANE IN TRIFLUOROACETIC ACID
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A mixture of thiols and aldehydes or ketones was converted into sulfides with pyridine-borane in trifluoroacetic acid.
- Kikugawa, Yasuo
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p. 1157 - 1158
(2007/10/02)
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