92822-55-4

Upstream product

• 80787-04-8 ethyl 2-(acetoxymethyl)acrylate 
• 931-51-1 cyclohexylmagnesiumchloride 
• 92822-43-0 ethyl 2-methylene-3-t-butylthiopropanoate 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 626-62-0 Cyclohexyl iodide 
• 17435-72-2 ethyl 2-bromomethyl-2-propenoate 
• 108-85-0 1-bromocyclohexane 
• 108286-71-1 ethyl-2-tributylstannylmethyl acrylate 
• 182123-98-4 2-carboethoxy allyl tris(trimethylsilyl)silane 
• 110-82-7 cyclohexane 
• 201230-82-2 carbon monoxide 
• 210489-88-6 ethyl 2-methylene-3-[(trifluoromethyl)sulfonyl]propanoate 
• 132627-71-5 2-[(4-methylphenylsulfonyl)methyl]propenoic acid ethyl ester 
• 98-89-5 Cyclohexanecarboxylic acid 

Downstream Products

• 89022-01-5 2-Acetylsulfanylmethyl-3-cyclohexyl-propionic acid 
• 131330-80-8 3-Cyclohexyl-2-methylenepropanoic acid 

Relevant academic research and scientific papers

Bromine-Radical-Mediated Site-Selective Allylation of C(sp 3)-H Bonds

The C(sp 3)-H allylation of alkanes is investigated by using allyl bromides under radical reaction conditions. In many cases, methine C-H allylation preceded methylene and methyl C-H allylation with complete or a high degree of site selectivity

Silver-Catalyzed Decarboxylative Allylation of Aliphatic Carboxylic Acids in Aqueous Solution

Direct decarboxylative radical allylation of aliphatic carboxylic acids is described. With K2S2O8 as the oxidant and AgNO3 as the catalyst, the reactions of aliphatic carboxylic acids with allyl sulfones in aqueous CH3CN solution gave the corresponding alkenes in satisfactory yields under mild conditions. This site-specific allylation method is applicable to all primary, secondary, and tertiary alkyl acids and exhibits wide functional group compatibility.

Organic photoredox catalysis for the oxidation of silicates: Applications in radical synthesis and dual catalysis

Metal free photooxidation of alkyl bis(catecholato)silicates with the organic dye 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyano-benzene (4CzIPN) allows the smooth formation of alkyl radicals. The latter can be efficiently engaged either with radical acceptors to provide homolytic addition products or in photoredox/nickel dual catalysis reactions to obtain cross-coupling products.

Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds

This works introduces hypervalent bis-catecholato silicon compounds as versatile sources of alkyl radicals upon visible-light photocatalysis. Using Ir[(dF(CF3)ppy)2(bpy)](PF6) (dF(CF3)ppy=2-(2,4-difluorophenyl)-5-trifluoromethylpyridine, bpy=bipyridine) as catalytic photooxidant, a series of alkyl radicals, including highly reactive primary ones can be generated and engaged in various intermolecular homolytic reactions. Based on cyclic voltammetry, Stern-Volmer studies, and supported by calculations, a mechanism involving a single-electron transfer from the silicate to the photoactivated iridium complex has been proposed. This oxidative photocatalyzed process can be efficiently merged with nickel-catalyzed Csp2-Csp3 cross-coupling reactions.

Preparation of alkylmagnesium reagents from alkenes through hydroboration and boron-magnesium exchange

Tolerant: Alkylmagnesium reagents can be synthesized from alkenes through a sequence of hydroboration and subsequent boron-magnesium exchange using a method that tolerates different functional groups (see scheme). The resulting alkylmagnesium reagents can be used in carbon-carbon bond forming reactions, such as alkylation reactions or transition-metal-catalyzed cross-coupling reactions. Copyright

Trifluoromethyl 1-radical-mediated carbonylation of alkanes leading to ethynyl ketones

The carbonylation of alkanes 1 under radical-reaction conditions was examined by using ethynyl triflone A as the unimolecular chain-transfer (UMCT) reagent. Good to moderate yields of ethynyl ketones 2 were prepared by means of this three-component coupli

New orally active enkephalinase inhibitors: Their synthesis, biological activity, and analgesic properties

A series of (4s)-4-[(2S)-benzyl-3-mercaptopropionylamino]-4-(N- phenylcarbamoyl)-butyric acids has been identified as potent systemically active enkephalinase inhibitors. Structure-activity relationships (SAR) are discussed. Further chemical modification of the inhibitors was carried out in order to identify the inhibitors which are orally active in an animal model. Compounds of particular interest are the prodrug-like analogues, including 5b (ONO-9902). Their analgesic effects after oral administration were evaluated.

Use of allylic trifiones for allylation of C-H bonds

Allylic trifiones react with THF and cyclohexane and related molecules to undergo a trifluoromethyl radical mediated C-H functionalization reaction. Due to polar effects, the reactions benefit from the presence of electron- withdrawing group at the 2-position of the allylic trifiones.

Iodine-Zinc Exchange Reactions Mediated by i-Pr2Zn. A New Preparation of Secondary Zinc Reagents

By treatment with i-Pr2Zn, functionalized secondary alkyl iodides undergo a smooth iodine-zinc exchange reaction leading to polyfunctional secondary dialkylzinc derivatives. Remarkably, i-Pr2Zn generated in situ from i-PrMgBr and ZnBr2 undergoes this exchange reaction almost 200 times faster than salt free i-Pr2Zn and constitutes a practical source of i-Pr2Zn for the performance of exchange reactions.

2-Functionalized allyl tris(trimethylsilyl)silanes as radical-based allylating agents

Radical allylations with 2-functionalized allyl tris(trimethylsilyl)silanes occur under mild conditions in good to excellent yield provided that the radical precursor and the silane have the appropriate electronic pairing. These reactions offer tin-free alternatives for transformations that are currently conducted with allyl stannenes.