23128-65-6

Upstream product

• 31378-03-7 1-phenyl-2-tosylethanone 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 98-86-2 acetophenone 
• 70-11-1 α-bromoacetophenone 
• 1666-24-6 α-benzoyl-α-(p-tolylsulfonyl)diazomethane 
• 140156-00-9 1-methyl-4-(2-phenylallyl)benzene 
• 948-97-0 2,3-diphenyl-1-propene 
• 1433269-77-2 methyl 4-(2-phenylallyl)benzoate 
• 93273-60-0 1-methoxy-3-(2-phenylallyl)benzene 
• 1231245-70-7 C₁₅H₁₃Cl 
• 86148-32-5 2-phenyl-2-propen-1-ol benzoate 

Downstream Products

• 37891-95-5 bromomethyl 4-tolyl sulfone 
• 31378-03-7 1-phenyl-2-tosylethanone 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 

Relevant academic research and scientific papers

Copper-Catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon-Carbon Bonds of 1,1-Disubstituted Alkenes with Sulfonyl Hydrazides

Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations. However, carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen, is scarce and underdeveloped. Herein, we report alkoxy radical, which was generated from alkyl radical and dioxygen, mediated selective cleavage of unstrained carbon-carbon bond for the oxysulfonylation of 1,1-disubstituted alkenes, providing facile access to a variety of valuable β-keto sulfones. Mechanistic experiments indicated alkoxy radical intermediate that underwent subsequent regioselective β-scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C—C bond cleavage. Notably, the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.

NBS-mediated synthesis of β-keto sulfones from benzyl alcohols and sodium arenesulfinates

An efficient synthetic route towards the synthesis of β-keto sulfones has been developed from secondary benzyl alcohols using N-bromosuccinimide (NBS). The present protocol utilizes NBS as oxidant as well as brominating agent, readily accessible benzyl alcohols and sodium arenesulfinates as the sulfonylating reagent under mild conditions. The control experiments revealed that the reaction proceeds via oxidation of alcohol to ketone, α-bromination of ketone and nucleophilic substitution by sodium arenesulfinate. Furthermore, the efficiency of the methodology was tested with a gram scale reaction and also shown the synthetic utility.

Copper Triflate Mediated α-Monohalogenation of α-Diazo β-Ketosulfones with Ammonium Halides

Copper triflate mediated α-monohalogenation of α-diazo β-ketosulfones with ammonium halides provides the corresponding α-halo β-ketosulfones. Different metal triflates are investigated for this facile and efficient transformation. A plausible mechanism is proposed.

Copper Acetate Mediated α-Oxysulfonylation of α-Diazo β-Ketosulfones

Copper acetate mediated α-oxysulfonylation of α-diazo β-ketosulfones in wet nitromethane under nitrogen provides α-oxysulfonyl β-ketosulfones. The use of different copper salts is investigated for the development of a facile and efficient transformation.

Chemoselective mono halogenation of β-keto-sulfones using potassium halide and hydrogen peroxide; synthesis of halomethyl sulfones and dihalomethyl sulfones

The synthesis of α-halo β-keto-sulfones using potassium halide and hydrogen peroxide as a chemoselective mono halogenation reagent and the synthesis of α,α-symmetrical and asymmetrical dihalo β-keto-sulfones and α-halo, α-alkyl and β-keto-sulfones is described. Base induced cleavage of α-halo β-keto-sulfones, α,α-dihalo β-keto-sulfones, and α-halo, α-alkyl β-keto-sulfones afforded the corresponding halomethyl sulfones, dihalomethyl sulfones and haloalkyl sulfones.

Rapid and convenient synthetic strategy for 2-amino-4-aryl-5-aryl-sulfonyl thiazoles

Synthesis of 2-amino-4-aryl-5-arylsulfonyl thiazoles 2a-i have been successfully carried out in one pot by condensing α-aryl sulfonyl-4-substituted acetophenones with phenyl trimethyl ammonium tribromide (PTT) and thiourea. The required α-aryl sulfonyl-4-substituted acetophenones have also been prepared by modified one pot method.