Iron(iii)-catalyzed aerobic dioxygenation of styrenes using N-hydroxyphthalimide and N-hydroxybenzotriazole?

Organic & Biomolecular Chemistry Pub Date: 2016-02-17 DOI: 10.1039/C6OB00210B

Abstract

Iron-catalyzed dioxygenation of alkenes in air using N-hydroxyphthalimide (NHPI) and N-hydroxybenzotriazole (HOBt) is described at room temperature. The products can be readily converted into 1,2-vicinal diols using PPh3 and Mo(CO)6. The use of Fe(NO3)3·9H2O as the catalyst, mild reaction conditions and the selectivity are the significant practical features. The radical scavenger experiment suggests that the reaction proceeds via a radical intermediate. The synthetic and mechanistic aspects have been presented.

Graphical abstract: Iron(iii)-catalyzed aerobic dioxygenation of styrenes using N-hydroxyphthalimide and N-hydroxybenzotriazole
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