59807-90-8

Upstream product

• 3112-85-4 methylphenylsulfonate 
• 104-88-1 4-chlorobenzaldehyde 
• 1073-67-2 4-vinylbenzyl chloride 
• 80-17-1 benzenesufonyl hydrazide 
• 98-09-9 benzenesulfonyl chloride 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 38488-19-6 1-(4-chlorophenyl)-2-(phenylsulfonyl)ethanone 
• 873-55-2 sodium benzenesulfonate 

Downstream Products

• 34101-22-9 (E)-4-chlorostyryl phenyl sulfone 
• 66022-86-4 [2-Benzenesulfonyl-1-(4-chloro-phenyl)-ethyl]-dimethyl-amine 

Relevant academic research and scientific papers

Efficient synthesis of an apremilast precursor and chiral β-hydroxy sulfones via ketoreductase-catalyzed asymmetric reduction

Ketoreductase (KRED)-catalyzed asymmetric reduction of prochiral ketones is an attractive method to synthesize chiral alcohols. Herein, two KREDs LfSDR1-V186A/E141I and CgKR1-F92I with complementary stereopreference were identified towards reduction of apremilast prochiral ketone intermediate 1a. LfSDR1-V186A/E141I exhibited >99% conversion and 99.2% ee yielding an apremilast chiral alcohol intermediate ((R)-2a) at 50 g L?1 substrate loading. Furthermore, we investigated the substrate scope of β-keto sulfones by using LfSDR1-V186A/E141I and CgKR1-F92I to produce both enantiomers of the corresponding β-hydroxy sulfones, with good-to-excellent conversion (up to >99%) and enantioselectivity (up to 99.9% ee) being obtained in most cases. Finally, the gram-scale synthesis of (R)-2a was performed by employing the crude enzyme of LfSDR1-V186A/E141I and BsGDH to afford the desired enantiomer with >99% conversion, 85.9% isolated yield and 99.2% ee. This study presents a biocatalytic strategy to synthesize chiral β-hydroxy sulfones.

Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants

2-Aryl-1-sulfonyl-substituted cyclobutanes were prepared in an intermolecular [2 + 2] photocycloaddition from various α,β-unsaturated sulfones and olefins upon irradiation at λ = 300 nm (26 examples, 60-99% yield). Lewis acids catalyzed the [2 + 2] photocycloaddition of 2-benzimidazolyl styryl sulfones. At short wavelengths, the latter substrates underwent C-S bond cleavage but AlBr3 (5 mol %) allowed for an intermolecular reaction with 2,3-dimethyl-2-butene at longer wavelengths. A chiral-at-metal Lewis acid (2 mol %) facilitated an enantioselective reaction (up to 77% ee).

Iodine-Triggered Aerobic Oxysulfonylation of Styrenes

An iodine-triggered dioxygen activation in oxysulfonylation reactions of unactivated olefins using sulfonyl hydrazides and iodine as catalyst is reported here. In one pot, near quantitative syntheses of β-hydroxysulfones were achieved at 70 °C, within 7 h, in acetonitrile and under aerobic conditions. A plausible mechanism is established by radical trapping and 18O labelling experiments for the operationally simple, efficient and economically viable transformation. The direct activation of aerial oxygen under metal-free and mild conditions is proposed for the oxysulfonylation of olefins. (Figure presented.).

Molecular-iodine-catalyzed aerobic oxidative synthesis of β-hydroxy sulfones from alkenes

The synthesis of β-hydroxy sulfones from alkenes and sodium sulfinates under aerobic oxidative conditions was achieved in the presence of a catalytic amount of molecular iodine. Molecular oxygen in air serves as the terminal oxidant and the catalytic amount of molecular iodine acts as the sulfonyl radical initiator and peroxide reductant. This journal is the Partner Organisations 2014.