69393-87-9

Upstream product

• 109-72-8 n-butyllithium 
• 62158-92-3 (2,2,2-trifluoroethyl) (4-methylphenyl) sulfide 
• 103-19-5 di(p-tolyl) disulfide 
• 693-02-7 hex-1-yne 
• 106-45-6 para-thiocresol 
• 5720-05-8 4-methylphenylboronic acid 
• 933-00-6 p-methylbenzenesulfenyl chloride 

Downstream Products

• 127894-29-5 (Z)-1-(4-methylphenyl)sulfanyl-1-hexene 
• 127894-23-9 S-(4-methylphenyl) hexanethioate 
• 126856-08-4 1-(4-methylphenylthio)-2-hexanone 
• 1056280-07-9 C₂₀H₂₄S 
• 1217435-95-4 (Z)-1-benzoyl-1-(4-methylphenyl)thio-1-hexene 
• 1217435-98-7 (Z)-1-(4-chlorobenzoyl)-1-(4-methylphenyl)thio-1-hexene 
• 1070656-66-4 1-benzyl-5-n-butyl-4-(p-toluenesulfonyl)-1H-1,2,3-triazole 
• 1605324-09-1 1-benzyl-4-butyl-5-(p-tolylthio)-1H-1,2,3-triazole 
• 1070656-65-3 1-benzyl-4-n-butyl-5-(p-toluenesulfonyl)-1H-1,2,3-triazole 
• 1132096-04-8 (Z)-2-methyl-3-(4-methylphenyl)sulfanyl-3-octen-2-ol 
• 445282-52-0 (Z)-1-phenyl-2-(4-methylphenyl)sulfanyl-2-hepten-1-ol 
• 479623-81-9 (E)-1-(4-methylphenyl)sulfanyl-1-tributylstannyl-1-hexene 

Relevant academic research and scientific papers

Transition Metal-Free C-H Thiolation via Sulfonium Salts Using β-Sulfinylesters as the Sulfur Source

We disclose a direct C(sp)-, C(sp2)-, and C(sp3)-H thiolation reaction using β-sulfinylesters as the versatile sulfur source. The key step of this protocol is chemoselective C-S bond cleavage of the sulfonium salts that are formed in situ from the corresponding alkenes, alkynes, and 1,3-dicarboxyl compounds with β-sulfinylesters. The successful capture of the acrylate byproduct supports a retro-Michael reaction mechanism.

N-Alkynylthio Phthalimide: A Shelf-Stable Alkynylthio Transfer Reagent for the Synthesis of Alkynyl Thioethers

A new kind of electrophilic alkynylthiolating reagent, called N-alkynylthio phthalimide, is designed and synthesized herein. This electrophilic sulfenylating reagent can be easily prepared in three steps from commercially available phthalimide and corresp

Rhodium(I)-Catalyzed Regioselective Azide-internal Alkynyl Trifluoromethyl Sulfide Cycloaddition and Azide-internal Thioalkyne Cycloaddition under Mild Conditions

A regioselective method to access fully substituted 5-trifluoromethylthio-1,2,3-triazoles and 5-thio-1,2,3-triazoles from the internal alkynyl trifluoromethyl sulfides and internal thioalkynes by a rhodium(I)-catalyzed azide-alkyne cycloaddition (RhAAC) reaction under mild conditions has been developed. This approach features good compatibility with water and air, a broad substrate scope, good functional group tolerance, high yields and excellent regioselectivities. The high 1,5-regioselectivities were controlled by the strong coordination between the sulfur atom and the π-acidic rhodium. The advantages of this method further include its applicability to gram-scale preparation, the use of solid-phase synthesis technique, and the mutually orthogonal CuAAC-RhAAC reaction. (Figure presented.).

Regiodivergent Rhodium(I)-Catalyzed Azide-Alkyne Cycloaddition (RhAAC) to Access Either Fully Substituted Sulfonyl-1,2,3-triazoles under Mild Conditions

A regiodivergent Rh(I)-catalyzed azide-alkyne cycloaddition (RhAAC) was developed for the synthesis of both fully substituted 4-sulfonyl-1,2,3-triazoles and 5-sulfonyl-1,2,3-triazoles in high regioselectivities and yields under mild conditions in one step

Investigations on Gold-Catalyzed Thioalkyne Activation Toward Facile Synthesis of Ketene Dithioacetals

Nucleophilic addition to thioalkynes was investigated under various catalytic conditions with gold(I) complexes being identified as the optimal catalysts. Structural evaluation of the product revealed an unexpected cis-addition, arising from a gold-associated thioketene intermediate. Based on this interesting mechanistic insight, a gold(I)-catalyzed thioether addition to thioalkynes was developed as a novel approach to prepare ketene dithioacetals with good yields and high efficiency.

Iridium-catalyzed intermolecular azide-alkyne cycloaddition of internal thioalkynes under mild conditions

An iridium-catalyzed azide-alkyne cycloaddition reaction (IrAAC) of electron-rich internal alkynes is described. It is the first efficient intermolecular AAC of internal thioalkynes. The reaction exhibits remarkable features, such as high efficiency and r

Asymmetric claisen rearrangements on chiral vinyl sulfoxides

Highly diastereoselective Claisen rearrangements of acyclic allyl vinyl ethers bearing a chiral sulfoxide at C-5 provide γ-δ-unsaturated aldehydes or ketones with up to two consecutive asymmetric centers in the molecule whilst preserving a useful vinyl su

Ruthenium-catalyzed [2+2] cycloadditions of alkynyl sulfides and alkynyl sulfones

Ruthenium-catalyzed [2+2] cycloadditions of bicyclic alkenes with alkynyl sulfides and alkynyl sulfones were investigated. The sulfide and sulfone moieties were found to be compatible with the Ru-catalyzed cycloadditions, giving the corresponding cyclobut

Nucleophilic epoxidation of α′-hydroxy vinyl sulfoxides

The nucleophilic epoxidation of a variety of α′-(1-hydroxyalkyl) vinyl sulfones and sulfoxides has been studied. The sulfones give rise to anti oxiranes with modest (E) or excellent (Z) selectivities and in good yields. The (E)-sulfoxides display low reactivity within a reinforcing/nonreinforcing scenario. The use of t-BuOOLi in Et2O allows for a highly syn-selective epoxidation-oxidation. The (Z)-sulfoxides display a remarkably high reactivity under these conditions. The reinforcing (S,Ss) diastereomers (3e-g) yield hydroxy sulfinyl oxiranes with high yields and selectivities. In contrast, the (R,Ss) diastereomers (4e-g) show diminished reactivities and a very substrate-dependent stereochemical outcome. The structure of these oxiranes has been secured by chemical correlations and an X-ray crystal structure.

The hydroboration of 1-alkylthio-1-alkynes, and its application to the syntheses of s-alkyl alkanethioates and (Z)-1-alkylthio-1-alkenes

Hydroboration of 1-alkylthio-1-alkynes with dicyclohexylborane or bis(1,2-dimethylpropyl)borane proceeded smoothly, adding most of the dialkylboryl group to the α-position of the triple bond. The resulting alkenylboranes afforded either S-alkyl alkanethio