Photoredox-Catalyzed Cascade spe 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.

Automated summary

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