First Suzuki–Miyaura type cross-coupling of ortho-azidobromobenzene with arylboronic acids and its application to the synthesis of fused aromatic indole-heterocycles

A short synthesis of some fused indole-heterocycles has been achieved via Pd-catalyzed cross-coupling reactions between azido-2-bromobenzene and arylboronic acids and subsequent thermally induced nitrene insertion. Additionally, 4-amino-α-carboline, a versatile intermediate toward grossularine analogs has also been prepared by Suzuki–Miyaura cross-coupling of 4-pivaloylaminopyridine-3-boronic acid with 2-bromoaniline, followed by simple functional group transformations.