Copper(I) Bromide Catalyzed Arylation of Cyclic Enamides and Naphthyl-1-acetamides Using Diaryliodonium Salts

Abstract

Copper(I) bromide catalyzed direct C-H arylation of cyclic enamides was achieved using diaryliodonium salts in the absence of base/additive at ambient temperature with high yields. A biologically active dihydro[a]benzocarbazole scaffold was synthesized using the established protocol. The scope of the current methodology was further extended for the synthesis of C4-, C7-aryl-substituted 1-naphthyl acetamides in good yields.

Recent Advances in Alkenyl sp2 C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications

“…Of note, this reaction was conducted at room temperature without any base or additive, featuring a wide substrate scope with good to excellent yields (Scheme 279b). 455 In 2017, Zhang and co-workers elaborated a general approach for the synthesis of multisubstituted oxazoles by the tandem oxidative cyclization of acyclic enamides with aryl iodides (Scheme 280). 456 The reaction occurred via the amidedirected vinylic C−H arylation followed by a silver-mediated oxidative cyclization sequence, thus allowing the rapid assembly of 2,4,5-trisubstituted oxazoles from readily available starting materials.…”

Rhodium(III)-Catalyzed Direct C–H Arylation of Various Acyclic Enamides with Arylsilanes

“…Recently, the direct functionalization of enamides via olefinic β-C­(sp 2 )–H bond activation has attracted immense attention. A variety of direct C–H functionalization reactions such as alkylation, allylation, alkynylation, trifluoromethylation, acylation, arylation, and sulfonylation have been successively realized. Despite the significant advances achieved in the β-C­(sp 2 )–H arylation of enamides, these reactions are usually limited to cyclic enamides.…”

Diaryliodonium Salts in Organic Syntheses: A Useful Compound Class for Novel Arylation Strategies

“…In contrast, the cyclopentene 113 formation is notable for a The concept of aromatic electrophile generation via the intermediacy of a Cu(III) species was presented previously on several examples. [62][63][64][65][66][67][68][69][70][71][72][73][74][75][76][77][78][79][80][81] Utilizing this concept, several syntheses of diverse heterocyclic skeletons have been developed in the last few years in our and other laboratories. The copper-catalyzed synthesis of new oxazoline derivatives 115 from propargyl amides 114 and diaryliodonium salts was recently developed by our research group.…”

“…Kesavan et al 75 developed the copper bromide catalyzed arylation of cyclic enamide 98 and naphthyl-1-acetamide 99 using arylmesityliodonium salts in dichloromethane at room temperature (Scheme 38). The corresponding β-aryl cyclic enamides 100 and 101 were isolated in good yields (71-93%).…”