65885-28-1

Upstream product

• 936-59-4 3-chloropropiophenone 
• 873-55-2 sodium benzenesulfonate 
• 69267-23-8 trimethyl-(3-oxo-3-phenyl-propyl)-ammonium; bromide 
• 618-41-7 Benzenesulfinic acid 
• 22956-36-1 1-Phenyl-3-(phenylthio)-1-propanone 
• 768-03-6 Phenyl vinyl ketone 
• 19169-90-5 bromomethylphenylsulfone 
• 78386-38-6 1-tert-butoxy-1-phenylethene 
• 777882-10-7 α-1-adamantoxystyrene 
• 100-42-5 styrene 
• 65492-21-9 ((Iodomethyl)sulfonyl)benzene 
• 28143-79-5 1-phenyl vinyl triflate 
• 5535-48-8 PVS 
• 100-52-7 benzaldehyde 

Downstream Products

• 618-41-7 Benzenesulfinic acid 
• 768-03-6 Phenyl vinyl ketone 
• 167959-48-0 1-phenyl-3-(phenylsulfonyl)-propan-1-ol 

Relevant academic research and scientific papers

Rongalite as C1 Synthon and Sulfone Source: A Practical Sulfonylmethylation Based on the Separate-Embedding Strategy

Rongalite has been used in several challenging synthetic transformations with operationally simple and effective protocols. However, the employment of multiple characteristics of rongalite in synthetic chemistry is comparatively little known. Herein we report a separate-embedding type sulfonylmethylation of sulfoxonium ylides in which rongalite concurrently acted as a sulfone source, C1 synthon, radical initiator, and potential reducing reagent for the first time. Notably, this facile and easy-handling reaction does not require a catalyst or prefunctionalized sulfonylmethylation reagents.

Photochemical generation of acyl and carbamoyl radicals using a nucleophilic organic catalyst: Applications and mechanism thereof

We detail a strategy that uses a commercially available nucleophilic organic catalyst to generate acyl and carbamoyl radicals upon activation of the corresponding chlorides and anhydrides via a nucleophilic acyl substitution path. The resulting nucleophilic radicals are then intercepted by a variety of electron-poor olefins in a Giese-type addition process. The chemistry requires low-energy photons (blue LEDs) to activate acyl and carbamoyl radical precursors, which, due to their high reduction potential, are not readily prone to redox-based activation mechanisms. To elucidate the key mechanistic aspects of this catalytic photochemical radical generation strategy, we used a combination of transient absorption spectroscopy investigations, electrochemical studies, quantum yield measurements, and the characterization of key intermediates. We identified a variety of off-the-cycle intermediates that engage in a light-regulated equilibrium with reactive radicals. These regulated equilibriums cooperate to control the overall concentrations of the radicals, contributing to the efficiency of the overall catalytic process and facilitating the turnover of the catalyst. This journal is

Photoredox-Catalyzed Hydroacylation of Olefins Employing Carboxylic Acids and Hydrosilanes

A hydroacylation reaction of alkenes has been achieved employing readily available carboxylic acids as the acyl source and hydrosilanes as a hydrogen source via photoredox catalysis. The combination of both single electron transfer and hydrogen atom transfer steps has dramatically expanded new applications of carboxylic acids in organic synthesis. The protocol also features extremely mild conditions, broad substrate scope, and good functional group tolerance, affording a novel and convenient approach to hydroacylation of alkenes.

Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols

Tertiary cyclopropanols undergo ring-opening oxidative sulfonylation to afford γ-keto sulfones when reacting with sulfinate salts in the presence of a copper(ii) acetate catalyst and an oxidant (tert-butyl hydroperoxide or atmospheric oxygen). Various fluoroalkyl, aryl and alkyl sulfinate salts are successfully employed as sulfonylation reagents, affording the corresponding sulfones in up to 94% yields. The experimental protocol is mild and tolerates a number of functionalities in the cyclopropanol substrate. The reaction proceeds via a one-pot oxidation-Michael addition mechanism and can serve as a useful addition to the existing methods for the preparation of γ-keto sulfones based on the sulfa-Michael reaction.

Silver(I)-Promoted Radical Sulfonylation of Allyl/Propargyl Alcohols: Efficient Synthesis of γ-Keto Sulfones

An efficient Ag2CO3-promoted sulfonylation of allyl/propargyl alcohols with sodium sulfinates has been developed. The reaction tolerates a wide range of functional groups to deliver γ-keto sulfones in high yields (up to 93 %). Propargyl alcohols furnished trimerization product 1,3,5-triaroylbenzenes in the presence of sodium methanesulfinate under the standard conditions. A mechanism involving a sulfonyl radical was suggested.

Decarboxylative 1,4-Addition of α-Oxocarboxylic Acids with Michael Acceptors Enabled by Photoredox Catalysis

Enabled by iridium photoredox catalysis, 2-oxo-2-(hetero)arylacetic acids were decarboxylatively added to various Michael acceptors including α,β-unsaturated ester, ketone, amide, aldehyde, nitrile, and sulfone at room temperature. The reaction presents a new type of acyl Michael addition using stable and easily accessible carboxylic acid to formally generate acyl anion through photoredox-catalyzed radical decarboxylation.

Efficient synthesis of γ-keto sulfones by NHC-catalyzed intermolecular Stetter reaction

The N-heterocyclic carbene-catalyzed intermolecular Stetter reaction of aldehydes with α,β-unsaturated sulfones allows the atom-economic and selective formation of γ-keto sulfones in good yields. Key to the success of this unique transition-metal-free carbon-carbon bond-forming reaction is the right choice of the NHC precursor and base. The reaction tolerates a broad range of different aldehydes.

A tin-free, radical photocatalyzed addition to vinyl sulfones

Radical conjugate addition onto vinyl sulfones was achieved by means of a convenient, tin-free procedure. This was based on the photocatalyzed C-H bond activation in aldehydes, amides, ethers and even cycloalkanes by using tetrabutylammonium decatungstate

Radical alkylations of alkyl halides and unactivated C-H bonds using vinyl triflates

Radical alkylations of activated alkyl iodides and bromides were achieved using vinyl triflates in the presence of hexadimethyltin, whereas those of unactivated C-H bonds using vinyl triflates proceeded cleanly under tin-free conditions. Georg Thieme Verl

β-Keto sulfones as inhibitors of 11β-hydroxysteroid dehydrogenase type I and the mechanism of action

The design, synthesis, and biological evaluation of β-keto sulfones as 11β-HSD1 inhibitors and the mechanism of inhibition are described here. This class of compounds is not active against 11β-HSD2 and therefore may have therapeutic potential for metabolic syndrome and type 2 diabetes.