76173-08-5

Upstream product

• 76173-07-4 [1-(4-Bromo-phenyl)-pent-4-en-(E)-ylidene]-phenyl-amine 
• 3112-87-6 1-methyl-4-(prop-2-ene-1-sulfonyl)benzene 
• 1861-48-9 dithiocarbonic acid S-[2-(4-bromo-phenyl)-2-oxo-ethyl] ester O-ethyl ester 
• 878480-30-9 2-(4-bromobenzoyl)pent-4-enoic acid ethyl ester 
• 99-73-0 para-bromophenacyl bromide 
• 1730-25-2 allylmagnesium bromide 
• 346446-95-5 1-(4-bromo-phenyl)-pent-4-en-1-ol 
• 26510-95-2 ethyl 4-Bromobenzoylacetate 
• 68695-50-1 4-bromo-N-phenylbenzimidoyl chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 55991-66-7 1-(4-bromophenyl)-1-(trimethylsilyloxy)ethylene 
• 762-72-1 allyl-trimethyl-silane 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 586-75-4 4-chlorobenzoyl chloride 

Downstream Products

• 1001615-58-2 1-(p-Cyanophenyl)-4-pentene-1-one 
• 1210959-78-6 1-bromo-4-(hexa-1,5-dien-2-yl)benzene 

Relevant academic research and scientific papers

Radical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing N-Heterocycles via Dual Cobaloxime and Photoredox Catalysis

Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive molecules. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermolecular cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole products in satisfactory yields. In the presence of external alkenes, the tandem reaction generates E-selective coupling products with excellent chemo- and stereoselectivity.

Azido-Enolonium Species in C-C and C-N Bond-Forming Coupling Reactions

Vinyl azides react with boron trifluoride activated Koser's hypervalent iodine reagent to afford azido-enolonium species. These previously unknown azido-enolonium species react efficiently with aromatic compounds, allyltrimethylsilane, and azoles under mi

An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung

The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α-cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non-classical carbocations.

Saturated Bioisosteres of ortho-Substituted Benzenes

Saturated bioisosteres of ortho-disubstituted benzenes (bicyclo[2.1.1]hexanes) were synthesized, characterized and validated. These cores were incorporated into the bioactive compounds Valsartan, Boskalid and Fluxapyroxad instead of the benzene ring. The

Iron-catalyzed acylation-functionalization of unactivated alkenes with aldehydes

Herein, an iron-catalyzed acylation-functionalization of unactivated alkenes with aldehydes via distal group ipso-migration is reported. This strategy overcame the energy barrier and reversibility in the difunctionalization of unactivated alkenes with nuc

Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines

A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.

Palladium-Catalyzed Hydrocarbonylative Cyclization of 1,5-Dienes

A novel and atom-economic palladium-catalyzed isomerization-hydrocarbonylative cyclization reaction of 1,5-dienes to 2-alkylidenecyclopentanones has been developed, which provides a rapid and straightforward approach to 2-alkylidenecyclopentanones with high stereoselectivity. The reaction was found to proceed via alkene isomerization and selective hydrocarbonylative cyclization to generate 2-alkylidenecyclopentanones with high selectivity.

Visible-Light-Mediated Iminyl Radical Generation from Benzyl Oxime Ether: Synthesis of Pyrroline via Hydroimination Cyclization

The treatment of an O-(4-methoxybenzyl) oxime ether bearing an olefin substituent and 1-chloroanthraquinone (1-Cl-AQN) catalyst in 2-butanone under visible-light irradiation affords pyrroline via an iminyl radical intramolecular hydroimination. Mechanistic studies indicate that iminyl radical generation mainly proceeds by hydrogen abstraction of the photocatalyst from the benzyl position of the oxime. Moreover, the hydrogen atom was identified in circulation from the benzylic position of the substrates between AQN and 2-butanone to quench the carbon radical without requiring any additional reagents.

Oximinotrifluoromethylation of unactivated alkenes under ambient conditions

An efficient protocol for oximinotrifluoromethylation of unactivated alkenes was developed via trifluoromethyl radical-induced intramolecular remote oximino migration under mild reaction conditions, providing a wide range of β-trifluoromethylated oximes. Other fluoroalkyl radicals were also applicable for this transformation. This method provided access to synthetically challenging medium-sized ring scaffolds and the 6,7,5-fused lactam skeleton.

Enolonium Species—Umpoled Enolates

Enolonium species/iodo(III)enolates of carbonyl compounds have been suggested to be intermediates in a wide variety of hypervalent iodine induced chemical transformations of ketones, including α-C?O, α-C?N, α-C?C, and α-carbon–halide bond formation, but they have never been characterized. We report that these elusive umpoled enolates may be made as discrete species that are stable for several minutes at ?78 °C, and report the first spectroscopic identification of such species. It is shown that enolonium species are direct intermediates in C?O, C?N, C?Cl, and C?C bond forming reactions. Our results open up chemical space for designing a variety of new transformations. We showcase the ability of enolonium species to react with prenyl, crotyl, cinnamyl, and allyl silanes with absolute regioselectivity in up to 92 % yield.