This study demonstrates a photo-induced and tetrahydrofuran (THF)-based radical strategy for the selective oxidation of alkenes to carbonyls using O2 as the sole oxidant and water as the sole solvent.

A HFIP-promoted highly selective hydroxyalkylation of aniline derivatives with arylglyoxal hydrates has been realized. The reaction produces various N,N-dialkylanilines and their derivatives with α-hydroxy carbonyl units in good to excellent yields under mild conditions. Furthermore, the synthetic potential of this method has been demonstrated by the facile synthesis of several structurally interesting molecules such as benzil, 1,2,4-triazine, quinoxaline, hydantoin, and 2-thiohydantoin with aromatic amine units.

Hexafluoroisopropanol (HFIP) has been extensively applied in organic synthesis as a versatile reaction media. However, the application of HFIP as an catalyst in organic synthesis has been rarely studied. Presented here, is the example of HFIP‐catalyzed Mannich‐type reaction between quinoxalin‐2(1H)‐ones and difluoroenoxysilanes. The developed protocol tolerates various substituents under mild reaction conditions, providing a divergent approach to the construction of difluoro‐substituted 3,4‐dihydroquinoxalin‐2(1H)‐ones and monofluoroquinoxalin‐2(1H)‐ones in 51–92% yields.

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