Abstract
AbstractHerein, we report the identification of 2,3‐bis‐(2‐pyridyl) pyrazine as a new organocatalyst, which has been utilized for the direct cross‐coupling reactions of an aryl halide with unactivated arenes/heteroarenes via C(sp2)‐H bond activation. This transition metal‐free C−H arylation of unactivated benzenes with aryl halides (Ar−X; X=I, Br, Cl) underwent smoothly with only 10 mol% of an organocatalyst and in the presence of 3 equivalent of potassium tert‐butoxide base which furnished a library of biaryls (3 a–u) in up to 98 % excellent yield under milder reaction conditions. The mechanistic pathway involves the in‐situ formation of aryl radical anion intermediate and progressed via a single electron transfer (SET) mechanism. The wide substrate scope, high functional group forbearance, control/competition experiments, gram‐scale synthesis and kinetic studies signify the prominence and useful nature of the protocol along with the steadiness of the novel organocatalyst.
Published Version
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