89295-32-9

Usage

Uses

Used in Chemical Synthesis:
ETHYL-(2-PHENYLSULFOMETHYL)-ACRYLATE is used as a key intermediate in the synthesis of ethyl 2-[(1S,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]methylacrylate. This synthesis involves a radical allylation of β-alkylcatecholboranes, which is an important reaction in organic chemistry for the formation of carbon-carbon bonds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, ETHYL-(2-PHENYLSULFOMETHYL)-ACRYLATE may be utilized in the development of new drugs and drug candidates. Its unique structure and reactivity can be harnessed to create novel molecules with potential therapeutic applications.
Used in Material Science:
ETHYL-(2-PHENYLSULFOMETHYL)-ACRYLATE can also be employed in the field of material science, where it may be used to synthesize new polymers or other materials with specific properties. These materials could have applications in various industries, such as coatings, adhesives, or even in the development of new electronic devices.

Synthesis

Ethyl 2-((phenylsulfonyl)methyl)acrylate is synthesized from ethyl 2-(bromomethyl)acrylate.Step: To a solution of ethyl 2-(bromomethyl)acrylate (1.99 g, 10.4 mmol) in dry methanol (25 mL) was added sodium phenylsulfinate (2.50 g, 15.2 mmol). After 2.5 h of reflux the mixture was concentrated under reduced pressure, the obtained residue was dissolved in EtOAc and the mixture was washed with water, brine, dried with Na2SO4, filtered and the filtrate was evaporated and purified by chromatography (50% EtOAc/Petroleum ether) to give 35 as a viscous oil: Yield (1.94 g, 74%);1H NMR (400 MHz, CDCl3) δ 7.86 (d, J = 7.6 Hz, 2H), 7.64 (t, J = 7.6 Hz, 1 H), 7.54 (t, J = 7.6 Hz, 2H), 6.51 (s, 1H), 5.92(s, 1H), 4.17(s, 2H), 4.01(q, J = 7.2 Hz, 2H), 1.17(t, J = 7.2 Hz, 3H); 13C NMR (400 MHz, CDCl3) 164.73, 138.38, 133.86, 133.33, 129.11, 129.04, 128.77, 61.48, 57.52, 14.00.

Upstream product

• 140-88-5 ethyl acrylate 
• 10029-04-6 ethyl 2-(hydroxymethyl)acrylate 
• 873-55-2 sodium benzenesulfonate 
• 17435-72-2 ethyl 2-bromomethyl-2-propenoate 
• 50-00-0 formaldehyd 
• 97-63-2 methyl methacrylate 

Downstream Products

• 281-23-2 adamantane 
• 92822-54-3 ethyl 2-(adamantan-1-ylmethyl)acrylate 
• 108286-71-1 ethyl-2-tributylstannylmethyl acrylate 
• 14307-99-4 ethyl 2-methyl-4-phenyl butyrate 

Relevant academic research and scientific papers

Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines

A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.

Copper-Catalyzed Intermolecular Alkynylation and Allylation of Unactivated C(sp3)-H Bonds via Hydrogen Atom Transfer

We describe Cu-catalyzed intermolecular alkynylation and allylation of unactivated C(sp3)-H bonds with singly occupied molecular orbital-philes (SOMO-philes) via hydrogen atom transfer (HAT). Employing N-fluoro-sulfonamide as a HAT reagent, a set of subst

Silver-catalyzed decarboxylative radical allylation of α,α-difluoroarylacetic acids for the construction of CF2-allyl bonds

An efficient silver-catalyzed method of decarboxylative radical allylation of α,α-difluoroarylacetic acids to build CF2-allyl bonds has been developed. Using allylsulfone as an allyl donor, α,α-difluorine substituted arylacetic acids bearing various functional groups are successfully allylated to access a series of 3-(α,α-difluorobenzyl)-1-propylene compounds in moderate to excellent yields in aqueous CH3CN solution under the mild conditions. Experimental studies disclosed that the α-fluorine substitution of arylacetic acid has a great influence on free radical activity and reactivity.

Direct Decarboxylative Allylation and Arylation of Aliphatic Carboxylic Acids Using Flavin-Mediated Photoredox Catalysis

We describe herein a direct decarboxylative allylation of aliphatic carboxylic acids with allylsulfones using visible light and riboflavin tetraacetate (RFTA) as photocatalyst. The reaction proceeds at room temperature tolerating a wide range of functiona

Photoredox-Coupled F-Nucleophilic Addition: Allylation of gem-Difluoroalkenes

A novel strategy for the expedient construction of CF3-embeded tertiary/quarternary carbon centers was developed by taking advantage of photoredox catalysis. Thanks to a key step of single-electron oxidation, electron-rich gem-difluoroalkenes, which otherwise are essentially reluctant towards F-nucleoplilic addition, now readily participate in this fluoroallylation reaction. Furthermore, this strategy provides an elegant example for the generation, as well as functionalization, of α-CF3-substituted benzylic radical intermediates using cheap and readily available starting materials.

Photocatalytic Reductive Formation of α-Tertiary Ethers from Ketals

A general photocatalytic reductive strategy for the construction of unsymmetrical α-tertiary dialkyl ethers is reported. By merging Lewis acid-mediated ketal activation and visible-light photocatalytic reduction, in situ-generated α-alkoxy radicals were found to engage in addition reactions with a variety of olefinic partners. Good reaction efficiency is demonstrated with a range of ketals of aromatic and aliphatic ketones. Extension to acetal substrates is also described, demonstrating the overall synthetic utility of this methodology for complex ether synthesis.

Metal-Free C(sp3)-H Allylation via Aryl Carboxyl Radicals Enabled by Donor-Acceptor Complex

The first aryl carboxyl radical generation by the donor-acceptor complex with N-acyloxyphthalimides and Hantzsch esters is reported. Regio- and chemoselective C(sp3)-H bond allylation is enabled by aryl carboxyl radicals with visible light irradiation under mild and metal-free conditions.

N-Arylamines Coupled with Aldehydes, Ketones, and Imines by Means of Photocatalytic Proton-Coupled Electron Transfer

A photoredox-catalyzed umpolung strategy for coupling reactions between aldehydes, ketones, imines, and N-arylamines is reported. These reactions proceed by a Br?nsted acid-activated proton-coupled electron transfer pathway, and the protocol was used to synthesize a broad scope of 1,2-amino alcohols and vicinal diamines, both of which are common motifs in biologically active natural products, pharmaceutically active molecules, and ligands.

Donor–Acceptor Complex Enables Alkoxyl Radical Generation for Metal-Free C(sp3)–C(sp3) Cleavage and Allylation/Alkenylation

The alkoxyl radical is an essential and prevalent reactive intermediate for chemical and biological studies. Here we report the first donor–acceptor complex-enabled alkoxyl radical generation under metal-free reaction conditions induced by visible light. Hantzsch ester forms the key donor–acceptor complex with N-alkoxyl derivatives, which is elucidated by a series of spectrometry and mechanistic experiments. Selective C(sp3)-C(sp3) bond cleavage and allylation/alkenylation is demonstrated for the first time using this photocatalyst-free approach with linear primary, secondary, and tertiary alkoxyl radicals.

Generation of Alkoxyl Radicals by Photoredox Catalysis Enables Selective C(sp3)-H Functionalization under Mild Reaction Conditions

Reported herein is the first visible-light-induced formation of alkoxyl radicals from N-alkoxyphthalimides, and the Hantzsch ester as the reductant is crucial for the reaction. The selective hydrogen atom abstraction by the alkoxyl radical enables C(sp3)-H allylation and alkenylation reactions under mild reaction conditions at room temperature. Broad substrate variations, including a structurally complexed steroid, undergo the C(sp3)-H functionalization reaction effectively with high regio- and chemoselectivity.