jo060727r_si_001.pdf (9.33 MB)
Synthesis of Substituted Carbazoles, Indoles, and Dibenzofurans by Vinylic to Aryl Palladium Migration
journal contribution
posted on 2006-07-07, 00:00 authored by Jian Zhao, Richard C. LarockSubstituted carbazoles, indoles, and dibenzofurans are readily prepared in moderate to excellent yields
by the palladium-catalyzed cross-coupling of alkynes and appropriately substituted aryl iodides. This
process proceeds by carbopalladation of the alkyne, heteroatom-directed vinylic to aryl palladium migration,
and ring closure via intramolecular arylation or a Mizoroki−Heck reaction. Results from the deuterium
labeling experiments are consistent with the proposed mechanism.