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Photochemical Synthesis of Complex Carbazoles: Evaluation of Electronic Effects in Both UV‐ and Visible‐Light Methods in Continuous Flow

2015; Wiley; Volume: 21; Issue: 46 Linguagem: Inglês

10.1002/chem.201502661

1521-3765

Augusto C. Hernandez‐Perez, Antoine Caron, Shawn K. Collins,

Sulfur-Based Synthesis Techniques

Abstract An evaluation of both a visible‐light‐ and UV‐light‐mediated synthesis of carbazoles from various triarylamines with differing electronic properties under continuous‐flow conditions has been conducted. In general, triarylamines bearing electron‐rich groups tend to produce higher yields than triarylamines possessing electron‐withdrawing groups. The incorporation of nitrogen‐based heterocycles, as well as halogen‐containing arenes in carbazole skeletons, was well tolerated, and often synthetically useful complementarity was observed between the UV‐light and visible‐light (photoredox) methods.