Organic Photoredox Catalysis for Pschorr Reaction: A Metal-Free and Mild Approach to 6H-Benzo[c]chromenes

An expedient organic photoredox Pschorr reaction has been developed that opens up a synthetic route to 6H-benzo[c]chromenes. The process can be performed under mild conditions by using eosin Y as a photoredox catalyst and acetonitrile as the solvent. The diazonium salts can be either preformed or generated in situ from the corresponding amines with t-BuONO. The process is amenable to gram-sale synthesis of 6H-benzo[c]chromenes, which can be further transformed into both 6H-benzo[c]chromen-6-ones through oxidation or to 6H-benzo[c]chromen-6-amine through sp3 C–H bond amination. The protocol provides an attractive route for the synthesis of a library of 6H-benzo[c]chromes.

Azides – Diazonium Ions – Triazenes: Versatile Nitrogen-rich Functional Groups

For more than 100 years, nitrogen-rich compounds such as azides, diazonium ions, and triazenes have proved to be extremely valuable. Because these functional groups can be easily introduced into various substrates, they are frequently used nowadays. More importantly, they can be converted into a great number of other functional groups. The scope of this article is thus to summarize possible synthetic routes for the formation of these functional groups as well as to highlight some of the most prominent applications of these exciting moieties in chemical biology and combinatorial chemistry. Many of the most famous name reactions such as the Staudinger reduction, Staudinger ligation, Sandmeyer reaction, Wallach reaction, Mitsunobu reaction, Huisgen reaction, Balz–Schiemann reaction, Meerwein arylation, Pschorr reaction or Gomberg–Bachmann reaction are covered.