Synthesis of [1,2,3]Triazolo-[1,5-a]quinoxalin-4(5H)-ones through Photoredox-Catalyzed [3 + 2] Cyclization Reactions with Hypervalent Iodine(III) Reagents.

An efficient synthesis of a variety of [1,2,3]triazolo-[1,5-a]quinoxalin-4(5H)-ones via a [3 + 2] cyclization reaction by photoredox catalysis between quinoxalinones and hypervalent iodine(III) reagents is reported. A range of quinoxalinones and hypervalent iodine(III) reagents were tolerated well. This cyclization reaction allows access to structurally diverse [1,2,3]triazolo-[1,5-a]quinoxalin-4(5H)-ones in moderate to good yields.

Photoredox-Catalyzed Cascade sp2 C-H Bond Functionalization to Construct Substituted Acridine with Diarylamine and Hypervalent Iodine(III) Reagents.

A photocatalyzed cascade double C-C formation via sp2 C-H bond activation of diarylamines with hypervalent iodine diazo reagents was developed. A variety of diarylamines and hypervalent iodine(III) reagents were tolerated well, and a range of substituted acridines with yields ranging from moderate to excellent was provided efficiently. The protocol introduces diazo groups onto diarylamines and enables subsequent late-stage assembly point functionalization with the diazonium structure, forming two new C-C bonds in a sequential fashion.

Catalyst-Free Visible-Light-Promoted Cyclization of Aldehydes: Access to 2,5-Disubstituted 1,3,4-Oxadiazole Derivatives.

An efficient synthesis of a variety of 2,5-disubstituted 1,3,4-oxadiazole derivatives via a cyclization reaction by photoredox catalysis between aldehydes and hypervalent iodine(III) reagents is described. The reaction proceeds under mild conditions and affords various target compounds in excellent yields. The commercially available aldehydes without preactivation and a simple visible-light-promoted procedure without any catalysts make this strategy an alternative to the conventional methods.

Photoredox Catalysis Enables Decarboxylative Cyclization with Hypervalent Iodine(III) Reagents: Access to 2,5-Disubstituted 1,3,4-Oxadiazoles.

A novel approach to 2,5-disubstituted 1,3,4-oxadiazoles derivatives via a decarboxylative cyclization reaction by photoredox catalysis between commercially available α-oxocarboxylic acids and hypervalent iodine(III) reagent is described. This powerful transformation involves the coupling reaction between two different kinds of radical species and the formation of C-N and C-O bonds.