Visible-Light-Induced Difluoroalkylation of 1-(Allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-Arylvinyl)-2-(vinyloxy)benzenes: Synthesis of Bis-Difluoroalkylated Benzoxepines and 2H-Chromenes.

A novel visible-light-mediated difluoroalkylation of 1-(allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-arylvinyl)-2-(vinyloxy)benzenes for the synthesis of bis-difluoroalkylated benzoxepines and 2H-chromenes is developed. This method features mild reaction conditions, good regioselectivity, a wide substrate scope, good functional-group compatibility, and late-stage modification. Preliminary mechanistic studies reveal that the generation of the CF2CO2Et radical is more prone to reaction with the double bond of the aryl group.

Visible-Light-Induced Cascade Cyclization of N-Propargyl Aromatic Amines and Acyl Oxime Esters: Rapid Access to 3-Acylated Quinolines.

Visible-light-induced radical cascade acylation/cyclization/aromatization of N-propargyl aromatic amines and acyl oxime esters for the construction of 3-acylated quinolines is developed. This approach uses acyl oxime esters as the precursor of acyl radicals as well as acylation reagents, Eosin Y as the photocatalyst, and acetonitrile as the solvent, providing a convenient route toward 3-acylated quinolines via the C-C bond cleavage of acyl oxime esters.

Palladium-catalyzed radical cascade cyanoalkylsulfonylation/cyclization of 3-arylethynyl-[1,1'-biphenyl]-2-carbonitriles with cyclobutanone oxime esters and DABSO.

A palladium-catalyzed radical cascade cyanoalkylsulfonylation/cyclization of 3-arylethynyl-[1,1'-biphenyl]-2-carbonitriles with DABCO·(SO2)2 and cyclobutanone oxime esters via cleavage of a C-C single bond and insertion of SO2 was described. A series of cyanoalkylsulfone-containing cyclopenta[gh]phenanthridines were obtained in moderate-to-good yields, thus featuring mild reaction conditions, a broad substrate scope, and a high functional group tolerance.

Visible-Light-Induced Multicomponent Cascade Cycloaddition of N-Propargyl Aromatic Amines, Cyclobutanone Oxime Esters, and K2S2O5: Access to Cyanoalkylsulfonylated Quinolines.

A visible-light-induced cascade cyanoalkylsulfonylation/cyclization/aromatization of N-propargyl aromatic amines with K2S2O5 and cyclobutanone oxime esters for the construction of cyanoalkylsulfonylated quinolines is developed. This cascade transformation features mild reaction conditions, a broad substrate scope, and excellent functional group compatibility, providing a convenient route toward cyanoalkylsulfonylated quinolines via the formation of a C-C bond and two C-S bonds in one step.

Ni-Catalyzed radical cyclization of vinyl azides with cyclobutanone oxime esters to access cyanoalkyl containing quinoxalin-2(1H)-ones.

A nickel-catalyzed cascade addition/cyclization of 2-azido-N-arylacrylamides and cyclobutanone oxime esters for the construction of 3-cyanoalkylated quinoxalin-2(1H)-ones is developed. This reaction proceeds under mild conditions with good functional group tolerance and broad substrate scope. A preliminary mechanistic experiment indicated that the cyanoalkyl radical might be involved in this transformation.