110911-18-7

Upstream product

• 821-41-0 5-Hexen-1-ol 
• 4837-31-4 4-Phenylsulfanyl-morpholine 
• 882-33-7 diphenyldisulfane 
• 931-59-9 benzenesulfenyl chloride 
• 4972-31-0 1-benzenesulfinyl piperidine 
• 98-80-6 phenylboronic acid 
• 603-33-8 triphenylbismuthane 

Relevant academic research and scientific papers

Multicomponent Synthesis of Sulfones and Sulfides from Triarylbismuthines and Sodium Metabisulfite in Deep Eutectic Solvents

This study describes a novel and catalyst-free methodology for the multicomponent synthesis of a broad range of sulfones, disulfides, and sulfides from non-toxic triarylbismuthines (Ar3Bi) and sodium metabisulfite (Na2S2O5) in deep eutectic solvents (DESs). The fine tuning of the DESs properties allowed the solubility of all reagents, enhancing their reactivity, as well as, the recyclability of the reaction medium for at least 5 consecutive cycles. Thus, this versatile strategy uses non-toxic reagents without the need of metal catalysts in a sustainable solvent, being an interesting alternative to traditional hazardous protocols.

Evolution of a Polyene Cyclization Cascade for the Total Synthesis of (?)-Cyclosmenospongine

We report a full account on the development of a unique cationic polyene cyclization for the total synthesis of the tetracyclic meroterpenoid (?)-cyclosmenospongine. A highly convergent three-component coupling strategy enabled rapid access to individual cyclization precursors that were tested for their reactivity. The successful transformation generates three rings and sets four consecutive stereocenters in a single operation proceeding in a highly efficient manner to give exclusively the trans-decalin framework. In addition, we found that the enol ether geometry and the relative configuration of C3 and C8 are crucial for the success of the polyene cyclization.

Deep Eutectic Solvents as Reaction Media for the Palladium-Catalysed C?S Bond Formation: Scope and Mechanistic Studies

A unique jigsaw catalytic system based on deep eutectic solvents and palladium nanoparticles where C?S bonds are formed from aryl boronic acids and sodium metabisulfite, is introduced. The functionalization step is compatible with a broad spectrum of reagents such as nucleophiles, electrophiles or radical scavengers. This versatile approach allows the formation of different types of products in an environmentally friendly medium by selecting the components of the reaction, which engage one with another as pieces in a jigsaw. This simple procedure avoids the use of toxic volatile organic solvents allowing the formation of complex molecules in a one-pot reaction under mild conditions. Despite the fact that only 1 mol % of metal loading is used, the recyclability of the catalytic system is possible. Kinetic experiments were performed and the reaction order for all reagents, catalyst and ligand was determined. The obtained results were compared to palladium nanocrystals of different known shapes in order to shed some light on the properties of the catalyst.

Cyclofunctionalization of unsaturated alcohols, phenols, acids, and sulfonamides with 1-benzene-sulfinyl piperidine and trifluoromethanesulfonic anhydride

The combination of a benzenesulfinamide, trifluoromethanesulfonic anhydride, and Huenig's base brings about the cyclofunctionalization of unsaturated alcohols, phenols, acids, and sulfonamides to give the corresponding α-phenylsulfanylmethyl cyclic ethers, lactones and sulfonamides, respectively. In an unanticipated twist the products are isolated at the sulfur (II) oxidation state denoting an overall reduction in the oxidation state of the sulfur based electrophile in the course of the reaction.

INTRAMOLECULAR ARYLSULPHOETHERIFICATION AND LACTONIZATION OF UNSATURATED ALCOHOLS AND CARBOXYLIC ACIDS INITIATED BY ANODIC OXIDATION OF DISULPHIDES

The intramolecular sulphoetherification respectively sulpholactonization of alkenols and alkenoic acids can be initiated by addition of electrochemically generated sulphenyl cations starting from disulphides.The reaction can either be initiated by indirect electrochemical oxidation of diphenyldisulphide using bromide as redox catalyst or preferably by direct anodic oxidation of bis(4-methoxyphenyl)disulphide. 5- and 6-membered thioaryl substituted ethers and lactones thus may be generated starting preferably from mono or disubstituted alkenols and alkenoic acids.The reaction occurs as a trans-addition to the double bond while for endocyclic double bonds the new ring is cis-annelated.

PHENYLSULFENYL CHLORIDE/N,N-DIISOPROPYLETHYLAMINE: A USEFUL REAGENT FOR CYCLIC ETHER FORMATION (SULFENYLETHERIFICATION)

A general method for the formation of cyclic ethers and lactones is described.The procedure employs phenylsulfenyl chloride and N,N-diisopropylethylamine to generate an episulfonium ion intermediate from which the cyclic products arise by internal nucleophilic displacement.

CYCLIC ETHER SYNTHESIS: SULFENYLETHERIFICATION WITH BENZENESULFENYL CHLORIDE/N,N-DIISOPROPYLETHYLAMINE AND SULFENATE ESTER CYCLOADDITIONS

A general method for the formation of the cyclic ethers 9, 10, 13, 14, 16 and the lactone 30 is described.The procedure employs benzenesulfenyl chloride prepared in situ in acetonitrile and N,N-diisopropylethylamine to generate a thiiranium (episulfonium) ion intermediate from which the cyclic products arise by internal nucleophilic displacement.In the special case of the norbornene alcohols 1 and 2 the oxethanes 5 and 6 are formed by intramolecular sulfenate ester cycloaddition.

Cyclic Ether Formation with N-(Phenylthio)morpholine

Cyclic ethers with 5- to 7-membered rings are formed by sulphenoetherification of unsaturated alcohols with N-(phenylthio)morpholine and trifluoromethanesulphonic acid.