A photocatalytic decarboxylative/defluorinative reaction of α-trifluoromethyl alkenes with α-keto acids and α-amino has been developed. The occurs at room temperature under visible light irradiation, affording various γ,γ-difluoroallylic ketones 1,1-difluorohomoallyl amines in good yields. synthetic applications the resulting functionalized gem-difluoroalkenes were also described.

A mild and efficient method for the synthesis of 6-(trifluoromethyl)phenanthridines through oxidative cyclization 2-isocyanobiphenyls with CF3SiMe3 under metal-free conditions was developed. The reaction allows direct formation C-CF3 bonds rapid access to phenanthridine ring systems in one catalytic cycle.

Irradiation of hydrazines and 2-isocyanobiphenyls with visible-light in the presence organic dye eosin B generates various 6-substituted phenanthridines good yields.

A blue light-promoted cross-coupling of two distinct diazo compounds was described. The reaction produces E-configured trisubstituted alkenes in good yields the absence catalysts and additives. reactive free carbene intermediates were generated via selective photolysis one upon light irradiation.

Abstract A metal‐free, visible light‐induced [4+2] benzannulation of biaryldiazonium salts with alkynes was developed. With eosin Y as photoredox catalyst, a variety 9‐substituted or 9,10‐disubstituted phenanthrenes were obtained via cascade radical addition and cyclization sequence.

A first example of low-energy blue-light-mediated formal Doyle–Kirmse reaction for gem-difluoroallylation aryl diazoesters has been developed. variety highly functionalized gem-difluoroallyl containing esters bearing transformable sulfur and bromine groups were efficiently assembled with broad substrate scope under mild, catalyst-free, additive-free conditions. The represents a practical environmentally friendly approach C–CF2 bond formation based on rearrangement strategy, which will find...

The first visible-light induced cross-dehydrogenative coupling between tertiary amines and diazo compounds is described. reaction proceeds smoothly under mild metal-free conditions by using air or O2 as the oxidant, affording various β-amino-α-diazo adducts in moderate to good yields with broad substrate scopes. resulting products were successfully employed for synthesis of 4- 5-ester N-aryl-2,3-dihydrobenzo[d]azepines high regioselectivity simply switched selection transition metal catalysts.

Abstract A visible‐light‐mediated [3+3] annulation of tertiary amines with α‐trifluoromethyl alkenes was developed. The reaction offers a direct route to fluorinated tetrahydropyridines and azabicyclo[3.m.1] frameworks under very mild conditions. This protocol presents rare example dual sp 3 C−H functionalization the formation two different C−C bonds (one –sp bond, one 2 bond). Moreover, consecutive C−F substitutions in trifluoromethyl group were achieved pot using visible light photoredox...

Alkyl nitriles are versatile building blocks in organic synthesis because the cyano group can be easily converted into other functional groups. Iminyl-radical-triggered C–C bond cleavage of cycloketone oxime­ derivatives provides a practical route to access distal cyano-substituted alkyl radicals, which has given chemists new radical reaction platform for diverse nitriles. This review an overview various types cyanoalkylation via ring opening oxime derivatives. 1 Introduction 2 Bond...

A visible-light photoredox synthesis of 3-acylindoles through intramolecular oxidative cyclization o-alkynylated N,N-dialkylamines is developed. The reaction proceeds effectively under mild conditions using air as the oxidant, and only water generated a side product. plausible mechanism involving addition α-amino alkyl radicals to alkynes, followed by C-O bond formation, proposed.

Nitrogen heterocycles represent a highly important class of compounds which are widely used in materials science, agrochemistry, and medicinal chemistry. Therefore, there is continuing interest the development convenient, efficient, environmentally benign synthetic methods for construction nitrogen containing heterocycles. Due to its natural abundance, ease use, promising application industry, use visible light as driving force chemical reactions has received considerable attention past few...

A simple and efficient method for the synthesis of 2-trifluoromethyl quinolines by means visible-light-induced radical cyclization trifluoroacetimidoyl chlorides with alkynes has been developed. This protocol allows generation imidoyl radicals activation C(sp2)Cl bonds using a photoredox catalyst under mild environmentally friendly conditions (see scheme). As service to our authors readers, this journal provides supporting information supplied authors. Such materials are peer reviewed may...

Abstract An efficient method for the construction of fluorinated benzo[a]quinolizidines from α‐trifluoromethyl alkenes and dihydroisoquinoline acetic acids using visible light photocatalysis was developed. The reaction accomplished through a decarboxylative/defluorinative cross‐coupling, followed by an intramolecular defluorinative C−H functionalization in one‐pot. Diversified benzo[a]quinolizidines, which are less accessible other methods, were obtained good yields with high...

A general and practical method to synthesize 2-substituted benzofurans indoles is described. This employs easily accessible N-tosylhydrazones o-hydroxy or o-amino phenylacetylenes as substrates. The reaction proceeds through a CuBr-catalyzed coupling–allenylation–cyclization sequence under ligand-free conditions.

A simple and efficient method for the synthesis of benzazoles via Cu-catalyzed aerobic oxidative condensation o-amino/mercaptan/hydroxyanilines with benzylamines was developed.

Diazo compounds have been employed as the nucleophile in a silver-catalyzed three-component reaction with amines and 2-alkynylbenzaldehydes. Various 3-benzazepines were prepared one-pot manner based on cascade imine--yne cyclization/nucleophilic addition/1,2-aryl migration process. Moreover, this Ag(I)-mediated also provides practical route to diazo-containing dihydroisoquinolines under slightly modified conditions.

A novel silver-catalyzed cascade radical isonitrile insertion and defluorinative cyclization have been developed to synthesize CF2H- phosphinoyl-containing quinolines from ortho-isocyanyl α-trifluoromethylstyrenes. The reaction proceeded under redox-neutral conditions allowed the construction of a highly attractive quinoline ring system, with simultaneous formation CF2H group introduction various phosphinoyl groups in single transformation, showing operational simplicity, wide substrate...

Abstract In light of the extensive application fluoroalkyl‐containing molecules and functionalized quinoxalin‐2(1 H )‐ones in medicinal chemistry functional materials, visible‐light‐enabled C3‐H fluoroalkylation has garnered significant attention. this review, we provide a detailed overview latest advancements rapidly evolving research area. We cover utilization various fluoroalkyl sources under conditions photocatalyst or without photocatalyst, discuss pertinent reaction conditions,...

A base‐promoted three‐component carbonylative coupling reaction involving α‐trifluoromethyl styrenes, TosMIC, and alkyl halides is declared. TosMIC utilized as a commercially available CO source in this strategy. The good functional group tolerance, broad substrate scope simple operation demonstrate the universality practicality of method. 18O labeling experiment demonstrated that oxygen atom carbonyl originated from water.

A facile synthesis of gem-difluorinated fused quinolines via visible light-mediated cascade radical cyclization between functionalized difluoromethyl chlorides and alkenes was developed. Various highly were assembled in moderate to good yields under very mild reaction conditions. The extends the applications chlorodifluoroacetic acid as gem-difluoromethylenated building block by simple derivatization, especially heterocyclic rings, which are difficult access with existing methods.

A visible-light induced intramolecular radical cyclization is described. The reaction allows the rapid construction of 2-trifluoromethyl-3-acylindoles in a sequential C–C and C–O bond formation process under mild conditions.

By carefully choosing the reaction conditions, we have developed controllable FeCl3- or CuCl2-mediated dehydrazinative hydrogenation chlorination of 3,3-difluoroallyl hydrazines to access α-CF2H α-CF2Cl styrenes. The current provides for first time a facile method direct and selective synthesis styrenes starting from same precursors, which is easy scale up displays broad substrate scope good functional group tolerance. Moreover, product derivatization experiments demonstrated that resulting...

Open AccessCCS ChemistryRESEARCH ARTICLE1 Feb 2022External Photocatalyst-Free Visible Light-Promoted 1,3-Addition of Perfluoroalkyl Iodides to Vinyldiazoacetates Weiyu Li†, Xiaoyu Zhou†, Tiebo Xiao, Zhuofeng Ke and Lei Zhou Li† School Chemistry, Materials Science Engineering, Sun Yat-sen University, Guangzhou 510006 , Zhou† Xiao *Corresponding authors: E-mail Address: [email protected] https://doi.org/10.31635/ccschem.021.202000713 SectionsSupplemental MaterialAboutAbstractPDF ToolsAdd...

A base-promoted one-pot, three-component reaction of TosMIC with α -trifluoromethyl alkenes and alkyl halides has been deveolped for the synthesis isocyano-containing, densely functionalised gem -difluoroalkenes.