65645-46-7

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 108-98-5 thiophenol 
• 100-52-7 benzaldehyde 
• 91787-22-3 phenyl(phenylsulphonyl)trimethylsilylmethane 
• 368-43-4 phenylsulfonyl fluoride 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 3112-88-7 Benzyl phenyl sulfone 
• 831-91-4 Benzyl phenyl sulfide 
• 103904-52-5 1-acetoxy-2-(phenylthio)-1,2-diphenylethane 
• 98-80-6 phenylboronic acid 
• 4525-46-6 benzyltrimethylammonium iodide 
• 90083-21-9 1-acetoxy-2-(phenylsulfonyl)-1,2-diphenylethane 

Downstream Products

• 501-65-5 diphenyl acetylene 
• 103-30-0 (E)-1,2-diphenyl-ethene 

Relevant academic research and scientific papers

Cobalt-Catalyzed Redox-Neutral Sulfonylative Coupling from (Hetero)aryl Boronic Acids, Ammonium Salts and Potassium Metabisulfite

An efficient cobalt-catalyzed redox-neutral sulfonylative coupling to afford (hetero)aryl alkyl sulfones from boronic acids, ammonium salts and potassium metabisulfite has been realized. Commercially available and air-stable CoCl2, in combination with phenanthroline ligand, is sufficient to achieve rapid and high-yielding conversion of the reactants into the corresponding sulfones. This practical transformation proceeds smoothly through C?N bond cleavage under redox-neutral catalytic conditions and shows broad functional-group tolerance. Other carbon based electrophiles, including diaryliodonium salts, heteroaryl halides, and carbonates were compatible. Further transformation of aryl alkyl sulfones then allows conversion into olefins, alkenyl sulfones and halogenated sulfones, respectively, in a one-pot process.

Syntheses of diarylethenes by perylene-catalyzed photodesulfonylation from ethenyl sulfones

Diarylethenes were obtained from the corresponding ethenyl sulfones by photocatalyzed desulfonylation using UV or blue LEDs. When perylene and i-Pr2NEt were used as a photocatalyst and a sacrificing reagent, respectively, this desulfonylation proceeded smoothly to afford the desired ethenes with the functional groups such as chloro, alkoxy and heteroaromatic rings remaining untouched. The use of a flow photoreactor enabled this desulfonylation to proceed more rapidly to finish in an hour of residence time.

Studies of the condensation of sulfones with ketones and aldehydes

The condensation of ketones or aldehydes with sulfunes was shown to give a variety of products. Condensation of 2-methylcyclohexanone with dimethyl sulfone using potassium t-butoxide as base gave useful yields of 1,2- dimethylenecyclohexane. Under the same conditions, cycloheptanone, 3-methyl-2-butanone, and 2-bulanone were converted to dienes. Remarkably, these reaction conditions converted acetophenone into p-terphenyl (10%) and (E)-1,4-diphenyl-3-penten-1-one (44%). Propiophenone was converted to 2′-methyl-p-terphenyl (61%). Using α-tetralone produced 1-methynaphthalene and naphthalene. No reaction took place with β-tetralone. Using diethyl sulfone with α-tetralone lead to pure naphthalene. Condensation of isobutyraldehyde and dimethyl sulfone using potassium t-butoxide gave isoprene in low yield. Using benzaldehyde and benzyl phenyl sulfone in N,N-dimethylcinnamide gave 1,2-diphenyl-1- phenylsulfonylethylene, N,N-dimethylcinnamide, and a complex condensation product. Only 1,2-diphenyl-1-phenylsulfonylethylene was obtained when the solvent was THF.

Automated synthesis: Utilization of MEDLEY in synthetic processes

A variety of reactions which are commonly used in synthetic chemistry are feasible with the automated synthesizer (MEDLEY). Air-sensitive organolithium and Grignard reagents as well as transition metal catalysts like Ni(0) and Pd(0) species are employable. The precise control of both the reaction temperature and the amount of added reagents enables to examine the dependence of chemical yields on the reaction temperature. Since the order of reagent addition is programmed and the reaction temperature is quickly tunable, sequential reactions can be conducted smoothly. An advanced control system was incorporated which allows a task to start immediately after the preceding one has finished. Owing to this function, the time for completing the multistep process can be minimized.

Direct sulfonylation of lithiated alkyl phosphonates with benzenesulfonyl fluoride; Facile method for preparation of α-sulfonyl alkyl phosphonates and vinyl sulfones

α-Sulfonyl phosphonates were synthesized by direct sulfonylation of lithiated alkyl phosphonates with benzenesulfonyl fluoride which have shown different reactivity from benzenesulfonyl chloride, generally known as a sulfonylating reagent.

Mechanistic Aspects and Profiles of the Double Elimination Reaction of β-Substituted Sulfones

The double elimination reaction of β-acetoxy or β-alkoxy sulfones was investigated in detail by employing some representative reactions.Successful isolation of reaction intermediates revealed the reaction path: the first step is elimination of the acetoxy group to afford a vinyl sulfone.The subsequent elimination of a phenylsulfonyl group from the vinyl sulfone gives acetylenes, while polyenes are formed in cases where isomerization of the vinyl sulfone to an allyl sulfone is possible prior to the second elimination.Besides these mechanistic considerations, general features are discussed in order to make clear the scope and limitations of this synthetically useful reaction.

Synthesis of Alkenes via Peterson Reaction

The α-phenylthiosilanes (2) have been used to prepare the α-silyl anions (1) by reaction with lithium naphthalenide; subsequent condensation with a carbonyl compound gave the alkene (8) via the Peterson reaction.The α-phenylthiosilanes (2) were prepared from n,n-bis(phenylthio)acetals (4) by reaction with lithium naphthalenide and chlorotrimethylsilane.The n,n-bis(phenylthio)acetals (4) were obtained, in turn, from 1,1-bis(phenylthio)acetals (5) by anion formation with butyl-lithium-N,N,N',N'-tetramethylethylenediamine complex in hexane followed by reaction with an alkyl halide.The Peterson reaction was also used to prepare vinyl sulphides (9) and vinyl sulphones (13).

Reactions of α-Silylsulphones

α-Silylsulphones have been utilised to prepare vinylsulphones via the Peterson reaction and ketones by alkylation, reduction, and sila-Pummerer rearrangement.