Abstract
AbstractIodoarenes and C−H heteroarenes are coupled to form a biaryl in the presence of an amide base generated in situ from tetramethylammonium fluoride (TMAF) and hexamethyldisilazane (HMDS) by homolytic aromatic substitution (HAS). This reaction can be used with electron‐rich, ‐deficient, and ortho‐substituted haloarenes. Both electron‐rich and ‐deficient C−H heteroarenes can also be utilized. Involvement of a radical intermediate was confirmed by radical inhibition experiments, deuterium‐labelling experiments, and EPR spectral measurements. Enhancement of the reactivity of electron‐rich N‐methylpyrrole was observed in the presence of electron‐poor phenazine or pyrazine.
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