- Visible-Light-Mediated Alkylation of Thiophenols via Electron Donor-Acceptor Complexes Formed between Two Reactants
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A metal-free, photocatalyst-free, photochemical system was developed for the direct alkylation of thiophenols via electron donor-acceptor (EDA) complexes (KEDA = 145 M-1) between two reactants, N-hydroxyphthalimide esters as acceptors and thiophenol anions as donors, in the presence of a tertiary amine. The EDA complexes in the reaction system have a broad range of visible-light absorption (400-650 nm) and can trigger the reaction effectively under sunlight.
- Cai, Yi-Ping,Nie, Fang-Yuan,Song, Qin-Hua
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p. 12419 - 12426
(2021/09/02)
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- Thioether ligand-enabled cationic palladium (II)-catalyzed electrophilic C-H arylation of α,β-unsaturated oxime ethers
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The use of the cationic palladium(II) catalyst realized electrophilic C-H arylation of α,β-unsaturated O-SEM oximes with arylboronic acids. This Pd-catalyzed electrophilic C-H arylation is facilitated by employing alkyl aryl thioether ligands, and optimization of the ligand structure greatly improves the yield. The resulting α,β-unsaturated oximes would provide access to multisubstituted heterocyclic compounds.
- Tamura, Osamu,Yamada, Takahiro,Hashimoto, Yoshimitsu,Tanaka Iii, Kosaku,Morita, Nobuyoshi
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p. 12315 - 12328
(2020/11/10)
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- Deprotonated Salicylaldehyde as Visible Light Photocatalyst
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Salicylaldehyde is established as an efficient visible light photocatalyst for the first time. Compared to other simple aldehyde analogies, salicylaldehyde has a unique deprotonative red-shift from 324 to 417 nm and gives rise to the remarkable increase of fluorescence quantum from 0.0368 to 0.4632, thus enabling salicylaldehyde as a visible light (>400 nm) photocatalyst. The experimental investigations suggest that the reactive radical species are generated by sensitization of the substrates by the deprotonated salicylaldehyde through an energy-transfer pathway. Consequently, the C-C cleaving alkylation reactions of N-hydroxyphthalimide esters proceed smoothly in the presence of as low as 1 mol % of salicylaldehyde under the visible-light irradiation, affording desired alkylation products with up to 99% yields. Application in visible-light induced aerobic oxidation of N-alkylpyridinium salts is also reported.
- Zhuang, Yan-Jun,Qu, Jian-Ping,Kang, Yan-Biao
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p. 4386 - 4397
(2020/03/05)
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- Synthesis of Thioethers and Thioesters with Alkyl Arylsulfinates as the Sulfenylation Agent under Metal-Free Conditions
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A study on the coupling of cycloalkanes with alkyl arylsulfinates has been performed. Using iodine as the catalyst, through C (Formula presented.) ?H bond activation and sulfinates reduction, a wide range of thioethers were produced in moderate to high yields. Additionally, various thiocarboxylic esters can also be produced by simply performing the reaction under CO pressure. Notably, this is the first report in which alkyl arylsulfinates were used as sulfenylation agents in a cross-coupling transformation.
- Li, Yahui,Zhu, Fengxiang,Wang, Zechao,Wu, Xiao-Feng
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supporting information
p. 3503 - 3507
(2016/12/26)
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- Metal-free preparation of cycloalkyl aryl sulfides via di-tert-butyl peroxide-promoted oxidative C(sp3)-H bond thiolation of cycloalkanes
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A concise thiolation of the C(sp3)-H bond of cycloalkanes with diaryl disulfides in the presence of the oxidant di-tert-butyl peroxide (DTBP) has been developed. This reaction, without using any metal catalyst, tolerates varieties of disulfides and cycloalkanes substrates, giving good to excellent chemical yields, and thus provides a useful approach to cycloalkyl aryl sulfides from unactivated cycloalkanes.
- Zhao, Jincan,Fang, Hong,Han, Jianlin,Pan, Yi,Li, Guigen
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supporting information
p. 2719 - 2724
(2014/09/29)
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- Syntheses of sulfides and selenides through direct oxidative functionalization of C(sp3)-H bond
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A new protocol for C-S and C-Se bond formation by the direct functionalization of the C(sp3)-H bond of alkanes under metal-free conditions was developed. Using tBuOOtBu as the oxidant, the reaction of disulfides or diselenides with alkanes gave sulfides or selenides in moderate to good yields. The method was very simple and atom-economical.
- Du, Bingnan,Jin, Bo,Sun, Peipei
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supporting information
p. 3032 - 3035
(2014/06/23)
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- Palladium-catalyzed thiolation of alkanes and ethers with arylsulfonyl hydrazides
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A new method for the preparation of alkyl aryl sulfides through direct oxidative thiolation of alkanes or ethers with arylsulfonyl hydrazides using di-tert-butyl peroxide (DTBP) as an oxidant catalyzed by Pd(OAc)2 has been reported. The C-H bonds in various alkanes or ethers were successfully converted into C-S bonds to yield the corresponding sulfides in moderate to good yields. the Partner Organisations 2014.
- Guo, Sheng-Rong,He, Wei-Ming,Xiang, Jian-Nan,Yuan, Yan-Qin
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p. 8578 - 8581
(2014/07/22)
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- Water-promoted highly selective anti-Markovnikov addition of thiols to unactivated alkenes
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The highly selective anti-Markovnikov addition of thiols to unactivated alkenes is demonstrated in water at room temperature without any additive. This is a very simple and efficient method for the synthesis of linear thioethers. Georg Thieme Verlag Stuttgart.
- Ranu, Brindaban C.,Mandal, Tanmay
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p. 925 - 928
(2008/02/02)
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- The first example of alpha-thiomagnesiums generated from dithioacetal monoxides with Grignard reagent; their properties and some synthetic applications.
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Dithioacetal monoxides were synthesized from aldehydes and cyclohexanone, and reaction of the dithioacetal monoxides with Grignard reagents was investigated. The dithioacetal monoxide synthesized from alkylaldehyde and 4-chlorobenzenethiol reacted with i-
- Satoh, Tsuyoshi,Akita, Kiyoshi
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p. 181 - 186
(2007/10/03)
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- Copper-mediated cross-coupling of aryl boronic acids and alkyl thiols
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matrix presented The cross-coupling of aryl boronic acids and alkanethiols mediated by copper(II) acetate and pyridine in anhydrous dimethylformamide affords aryl alkyl sulfides in good yield with a wide variety of substituted aryl boronic acids. The method is applicable to the synthesis of aryl sulfides of cysteine.
- Herradura, Prudencio S.,Pendola, Kathleen A.,Guy, R. Kiplin
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p. 2019 - 2022
(2007/10/03)
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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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