Two birds with one stone: one-pot simultaneous synthesis of 2,2,2-trifluoroethylphenanthridines and benzochromenones featuring the utilization of the byproduct of Togni's reagent

In this paper, a novel and efficient one-pot synthesis of 2,2,2-trifluoroethylphenanthridines ( 4 ) and benzochromenones ( 5 ) through three-component reactions of vinyl azides ( 1 ) with cyclic α-diazo carbonyl compounds ( 2 ) and Togni's reagent ( 3 ) is presented. In these cascade reactions, 3 acted not only as the source of a CF 3 radical to react with 1 and 2 to afford 4 , but also as the pool of o -iodobenzoic acid to couple with 2 to afford 5 . To our knowledge, this is the first example in which 4 and 5 were obtained in a one-pot manner, and the byproduct of Togni's reagent, o -iodobenzoic acid, was trapped in situ by another substrate to give valuable products instead of being eliminated as a waste. A one-pot simultaneous synthesis of 2,2,2-trifluoroethylphenanthridines and benzochromenones featuring the utilization of the byproduct of Togni's reagent is presented.