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A variety of electron-rich heterocycles can be arylated
using this methodology (Table 2). Thiophene and ben-zothiophene are reactive (entries 1-3). Both 1,2- and 1,3-oxazole derivatives can be arylated (entries 4 and 6-8).Benzofuran is diarylated in a reasonable yield (entry 5).
Thiazole and benzothiazole arylation is also successful
(entries 9 -12). In 2-substituted thiazoles, the aryl group is
introduced next to sulfur (entries 11 and 12). 1- n- Butylimi-dazole is arylated in the 5-position, with some diarylationproduct also formed (entry 13). 1-Methyl-1,2,4-triazole is selectively arylated in the 5-position (entry 14). Caffeine is
very reactive, and some of the products are of interest as adenosine receptor antagonists (entries 15 -17).
If C -H activation methodology is not used, the synthetic sequences
leading to these compounds require several steps instead of
a single step.Amide substitution is tolerated on both aryl
chloride and the heterocycle (entries 1 and 12), and the N -H
bond is not arylated.Chlorobenzoic acid esters can also be
used (entry 7). 2-Chloropyridines are reactive (entries 2 and
6), and the products of these arylations may find use as
chelating ligands. Both electron-rich and electron-poor aryl
chlorides can be used; however, as expected, electron-poor
chlorides are more reactive. Some steric hindrance is tolerated
on the heterocycle (entry 4) and aryl chloride (entry 16).
Arylation ofN-methylindole under the standard conditions
resulted in low conversion (ca. 20%).

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