Direct methylthiolation ofC-,S-, andP-nucleophiles with sodiumS-methyl thiosulfate

Liu, Fanmin

doi:10.1039/d2ob02056d

Cited by 4 publications

(5 citation statements)

References 79 publications

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“…The title compound was isolated by flash chromatography on silica gel by using mixed petroleum ether and ethyl acetate (v/v = 100:1). Yellow oil, 22.7 mg, yield: 61% (known compound 55 ). 1 H NMR (300 MHz, CDCl 3 ): δ 7.20−7.15 (m, 1H), 7.04−7.01 (m, 2H), 6.72−6.68 (m, 1H), 3.75 (s, 3H), 2.38 (s, 3H).…”

Section: -(3-methoxyphenyl)-2-methyldisulfane (3n)mentioning

confidence: 99%

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Selective C(sp³)–S Bond Cleavage of Thioethers to Build Up Unsymmetrical Disulfides

Yang,

Luo,

et al. 2023

J. Org. Chem.

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The selective C(sp 3 )−S bond cleavage of thioethers was first developed to prepare unsymmetrical disulfides by using electrophilic halogenation reagents. In this strategy, NBS (Nbromosuccinimide) achieves selective furfuryl C(sp 3 )−S bond cleavage of furfuryl alkylthioethers at room temperature. Meanwhile, NFSI (N-fluorobenzenesulfonimide) enables selective methyl C(sp 3 )−S bond cleavage of aryl and alkyl methylthioethers at an elevated temperature. Notably, the substrate scope investigation indicates that the order of selectivity of the C−S bond cleavage is furfuryl C(sp 3 )−S > benzyl C(sp 3 )−S > alkyl C(sp 3 )−S > C(sp 2 )− S bond. Moreover, this practical and operationally simple strategy also provides an important complementary way to access various unsymmetrical disulfides with excellent functional group tolerances and moderate to good yields.

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Section: -(3-methoxyphenyl)-2-methyldisulfane (3n)mentioning

confidence: 99%

Section: -(3-methoxyphenyl)-2-methyldisulfane (3n)mentioning

confidence: 99%

Selective C(sp³)–S Bond Cleavage of Thioethers to Build Up Unsymmetrical Disulfides

Yang,

Luo,

et al. 2023

J. Org. Chem.

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“…[42] 2023. [47] Treatment of terminal alkynes 17, sodium S-methyl thiosulfate 16 with CuSO 4 catalyst produced the corresponding alkynyl sulfides 9 or 18 in high yields. The direct methylthiolation of phenyl-substituted alkynes with electron-donating (Me, OMe, n-Pent) or electron-withdrawing (Cl, Br, CF 3 , NO 2 , CN, acetyl, F) groups proceeded smoothly to afford the corresponding alkynyl sulfides 9 d, 9 b, 9 g, 9 f, 9 i, 9 m, 18 a-18 d in 63-88 % yields.…”

Section: Thiolation Of Terminal Alkynesmentioning

confidence: 99%

“…Cu-Catalyzed direct methylthiolation of terminal alkynes. [47] the optimal conditions were obtained as following: a mixture of cysteine-containing peptide 19 (0.2 mmol), sulfonium salt 20 (0.3 mmol) and Et 3 N (0.3 mmol) in DMSO under 0.2 mL/min at rt. Treatment of tetra-O-acetylated 1-thio-β-D-glucopyranose 22, phenylethynyl(diphenyl)sulfonium 20 with Et 3 N in DMSO afforded product 23 in significant yields with wide functional group tolerance.…”

Section: S-alkynylation and Photochemical Transformation Of Ketoximesmentioning

confidence: 99%

Synthesis of Alkynyl Sulfides: Alkynyl Trifluoromethyl Sulfides and Thiocyanates

Zeng,

Yuan,

Jiao

et al. 2023

Eur J Org Chem

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Sulfur‐containing alkynes, are important starting materials and intermediates in organic reactions. Some of sulfur‐containing alkynes display interesting bioactivities and are potentially applied as drugs. Various synthetic methodologies towards sulfur‐containing alkynes have been developed, including C(sp)–S coupling, thiolation, S‐alkynylation, trifluoromethylthiolation, etc. In this review, the approaches towards alkynyl sulfides in recent 3 years, as well as to form alkynyl trifluoromethyl sulfides and alkynylthiocyanates were highlighted. Firstly, the property and application of alkynes were introduced. After presenting the superiority of sulfur‐containing alkynes, their synthetic methods were classified and presented in details. According to different kinds of sulfur‐containing alkynes, synthetic methodologies for alkynyl sulfides, alkynyl trifluoromethyl sulfides and alkynylthiocyanates were summarized and the proposed reaction mechanisms were demonstrated if available.

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“…6 Another attempt involving N-thiophthalimides and benzeneselenol, in the presence of a base, yielded a mixture of selenosulfides, diselenides, and disulfides. 7 Other reported methods include the use of potassium tert-butoxide as a catalyst, 8 sodium S-methyl sulfothioate as a sulfur source, 9 and chloramination. 10 However, the above-mentioned meth-ods show a limited application, presumably because of the instability of the starting selenol.…”

mentioning

confidence: 99%

Base-Catalyzed One-Pot Synthesis of Selenosulfides: A Base Basicity-Controlled Approach

Lee,

Sim,

Lee

2023

J. Org. Chem.

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We developed a novel and efficient sequential one-pot synthesis of selenosulfides via a base-catalyzed methodology utilizing readily available starting compounds, under mild reaction conditions. This method eliminated the need for excess oxidants or additives and simplified the synthesis procedure. Furthermore, organic amine bases served as exceptional catalysts for synthesizing the target products. The performance of a catalytic system depends on the basicity of the bases. The selection of suitable bases, based on their pK aH values, is crucial for the selective synthesis of selenosulfides without the formation of byproducts. This method provides a direct route for the preparation of selenosulfides, which are important scaffolds in organic chemistry.

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Direct methylthiolation ofC-,S-, andP-nucleophiles with sodiumS-methyl thiosulfate

Abstract: A practical and efficient methylthiolation that employed the typical Bunte salt, sodium S-methyl sulfothioate as sulfur source was described. This reagent could react with a variety of compounds such as...

Cited by 4 publications

References 79 publications

Selective C(sp³)–S Bond Cleavage of Thioethers to Build Up Unsymmetrical Disulfides

Selective C(sp³)–S Bond Cleavage of Thioethers to Build Up Unsymmetrical Disulfides

Synthesis of Alkynyl Sulfides: Alkynyl Trifluoromethyl Sulfides and Thiocyanates

Base-Catalyzed One-Pot Synthesis of Selenosulfides: A Base Basicity-Controlled Approach

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Direct methylthiolation ofC-,S-, andP-nucleophiles with sodiumS-methyl thiosulfate

Abstract: A practical and efficient methylthiolation that employed the typical Bunte salt, sodium S-methyl sulfothioate as sulfur source was described. This reagent could react with a variety of compounds such as...

Cited by 4 publications

References 79 publications

Selective C(sp3)–S Bond Cleavage of Thioethers to Build Up Unsymmetrical Disulfides

Selective C(sp3)–S Bond Cleavage of Thioethers to Build Up Unsymmetrical Disulfides

Synthesis of Alkynyl Sulfides: Alkynyl Trifluoromethyl Sulfides and Thiocyanates

Base-Catalyzed One-Pot Synthesis of Selenosulfides: A Base Basicity-Controlled Approach

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Selective C(sp³)–S Bond Cleavage of Thioethers to Build Up Unsymmetrical Disulfides

Selective C(sp³)–S Bond Cleavage of Thioethers to Build Up Unsymmetrical Disulfides