3467-73-0

Upstream product

• 14933-91-6 N-phenyl-benzenesulphenamide 
• 108-98-5 thiophenol 
• 822-67-3 Cyclohex-2-enol 
• 1521-51-3 rac-3-bromocyclohexene 
• 882-33-7 diphenyldisulfane 
• 931-59-9 benzenesulfenyl chloride 
• 110-83-8 cyclohexene 
• 188400-02-4 (+/-)-methylthiocarbamic acid O-(cyclohex-2-enyl) ester 
• 14032-03-2 ((1R,2R)-2-chlorocyclohexyl)(phenyl)sulfane 
• 133957-59-2 2-(trimethylsilyl)ethyl benzenesulfenate 

Downstream Products

• 134427-76-2 ethyl 2-(2-cyclohexen-1-yl)-2-(phenylthio)-3,3,3-trifluoropropionate 
• 87413-32-9 (cyclohex-2-enylsulfonyl)benzene 
• 13733-59-0 (E/Z)-methyl-3-(phenylthio) acrylate 
• 33141-61-6 (2-Cyclohexenyl)(phenyl)sulfoxid 
• 1403961-73-8 N-(cyclohex-2-en-1-yl)-4-methyl-N-(phenylthio)benzenesulfonamide 
• 618-41-7 Benzenesulfinic acid 
• 1165952-91-9 cyclohexa-1,3-diene 
• 1165952-92-0 cyclohexa-1,4-diene 
• 1541-25-9 3-amino-1-cyclohexene 

Relevant academic research and scientific papers

Ionic liquid/PPh3 promoted cleavage of diphenyl disulfide and diselenide: A straight-forward metal-free one-pot route to the synthesis of unsymmetrical sulfides and selenides

A metal-free cleavage of diphenyl disulfide and diphenyl diselenide has been achieved using ionic liquid/triphenyl phosphine (PPh3) and a convenient protocol for the one-pot synthesis of unsymmetrical sulfides and selenides by condensing 'in situ' generated thiolate or selenate anion with alkyl halides has been developed. In addition, 1,4-conjugate addition of the generated thiolate anions to activated alkenes has also been demonstrated. The ionic liquid, 1-methyl-3-pentyl imidazolium bromide, [pmIm]Br plays a crucial role in promoting the course of the reactions and shows superior activity and selectivity compared to other solvents. The [pmIm]Br has been reused for at least five times without appreciable loss of activity.

Base-Mediated Radical Borylation of Alkyl Sulfones

A practical and direct method was developed for the production of versatile alkyl boronate esters via transition metal-free borylation of primary and secondary alkyl sulfones. The key to the success of the strategy is the use of bis(neopentyl glycolato) diboron (B2neop2), with a stoichiometric amount of base as a promoter. The practicality and industrial potential of this protocol are highlighted by its wide functional group tolerance, the late-stage modification of complex compounds, no need for further transesterification, and operational simplicity. Radical clock, radical trap experiments, and EPR studies were conducted which show that the borylation process involves radical intermediates.

Silver Salt-Mediated Allylation Reactions Using Allyl Bromides

A facile, efficient, and chemoselective synthesis of allylic amides has been developed. Allyl bromides were used as the precursors activated by silver triflate. A Ritter-type reaction readily proceeded to give various allyl amides under mild conditions. The reaction protocol was also applicable to different nucleophilic partners to give a wide range of allyl-substituted products in the absence of a base.

Direct Allylic C(sp3)-H Thiolation with Disulfides via Visible Light Photoredox Catalysis

In spite of the wide utility of allyl thioethers, the direct catalytic allylic C(sp3)-H thiolation remains elusive. Herein, we report the direct allylic C(sp3)-H thiolation mediated by visible light photoredox catalysis. The use of in situ-generated thiyl radical from disulfide as a hydrogen atom transfer (HAT) reagent and a coupling partner enabled selective cleavage of the allylic C(sp3)-H bond followed by C(sp3)-S bond formation. The undesired hydrothiolation, a prevalent reaction from facile thiyl radical addition to olefins, was prevented by the immediate deprotonation of thiol under basic conditions. A wide range of diaryl disulfides and olefins participated in the reaction, producing allyl thioethers with high efficiency. Mechanistic investigations revealed the participation of the photocatalyst as a redox mediator, which was crucial for the transformation of the allyl radical into the allyl cation and further ionic coupling process. Based on the proposed mechanism, a limitation in the synthesis of alkyl allyl sulfide was solved with a rationally designed more reducible unsymmetrical disulfide, which makes the desired catalytic cycle operative.

Lithium-Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3-Sulfanyl-Oxetanes as Bioisosteres

3-Sulfanyl-oxetanes are presented as promising novel bioisosteric replacements for thioesters or benzyl sulfides. From oxetan-3-ols, a mild and inexpensive Li catalyst enables chemoselective C?OH activation and thiol alkylation. Oxetane sulfides are formed from various thiols providing novel motifs in new chemical space and specifically as bioisosteres for thioesters due to their similar shape and electronic properties. Under the same conditions, various π-activated secondary and tertiary alcohols are also successful. Derivatization of the oxetane sulfide linker provides further novel oxetane classes and building blocks. Comparisons of key physicochemical properties of the oxetane compounds to selected carbonyl and methylene analogues indicate that these motifs are suitable for incorporation into drug discovery efforts.

Catalyst-free imidation of allyl sulfides with chloramine-T and subsequent [2,3]-sigmatropic rearrangement

A facile synthesis of various allyl sulfonamides based on imidation of allyl sulfides with chloramine-T and subsequent [2,3]-sigmatropic rearrangement has been achieved without metal catalysts. The reaction completes smoothly within 10 min, providing excellent yields in environment friendly solvent of alcohol. Functional groups such as bromine, hydroxyl, protected amido and aldehyde are tolerant under this condition.

Synthesis of allylic sulfides via cleavage of S-S bonds promoted by zinc metal in DMF

Cleavage of S-S bonds was achieved without any activation or catalysis, with a Zn/DMF system and subsequent treatment with allylic bromide afforded allylic sulfides in good to excellent yields.

Lanthanide complexes in organic synthesis: Synthesis of ethers from allyl alcohols

Coordinatively unsaturated lanthanide ions catalyze a wide variety of organic reactions. The hepta coordinated Ln(III) complexes with N,N′-ethylene-bis-(2-aminobenzamide) [EBAB] and N,N′ -propylene-bis-(2-aminobenzamide) [PBAB], the [Ln(EBAB)Cl3/sub

Aromatic Allylsulfenylation with in Situ Generated Allylic Thiols under the Heck Conditions

A wide structural variety of S-allylic thiocarbamates 2 can be prepared in good yields by the rearrangement of O-allylic thiocarbamates 1 under three different conditions: thermal activation (neat, 120-150°C), palladium(0) (25-65 °C), and palladium(II) catalysis (25-65°C). Of the two possible regioisomers of unsymmetrical S-allylic thiocarbamates 2, those of higher thermodynamic stability can be prepared in high purity under either thermal activation or palladium(0) catalysis. Although the thermodynamically less stable regioisomers of 2 are, in general, hard to be prepared in high purity, some of them (e.g., 2d and 2h′) can be obtained with an exclusive or high selectivity by the catalysis of palladium(II). The stereoisomeric pair of 2j and 2j′ can be prepared selectively by the palladium(0)-catalyzed rearrangement of 1j and 1k, respectively. These reactions proceed with retention of configuration at the allylic stereocenters, S-Allylic (2) and S-alkyl thiocarbamates (7) undergo fragmentation to generate thiolates in the presence of inorganic bases (e.g., K2CO3, K2CO3·-Et4N+I-) by heating in an aprotic solvent; the thus-formed thiolates react with aromatic iodides and vinyl bromides in the presence of palladium(0) complexes to furnish aryl and vinyl sulfides, respectively. A wide variety of aryl sulfides can be prepared in good yields irrespective of the kind of substituents and their substitution positions (o-, m-, p-) under conditions B [Pd(OAc)2, PPh3, K2CO3·Et4N+I-, dioxane, 100°C]. Under conditions E [Pd(OAc)2, PPh3, Cs2CO3, dioxane, 100°C], better yields result specifically for the sulfenylation of aromatic iodides bearing substituents having large Hammett σ constants.

Synthesis of 2-(Trimethylsilyl)ethyl Benzenesulfenate and Benzeneselenenate and Their Reaction with Some Electrophiles in the Presence of Tetrabutylammonium Fluoride

2-(Trimethylsilyl)ethyl benzenesulfenate was allowed to react with several halides in the presence of tetrabutylammonium fluoride (TBAF) to afford the corresponding phenyl sulfoxides as the main product.In the reaction of 2-(trimethylsilyl)ethyl benzeneselenenate and several halides with TBAF, the corresponding alcohols were obtained as the main product.