Table 2.

Electron-poor Heterocycle Arylation^a

entry	heterocycle	aryl halide/base	product	yield, %
1b		C6H5I/tBuOLi		58
2				41
3		C6H5I/tBuOLi		43
4				80
5				91
6		C6H5I/Et3COLi		60
7		C6H5I/Et3COLi		31

^aCopper (I) iodide (0.1 mmol), phenanthroline (0.1 mmol), aryl halide (1–2 mmol), heterocycle (1–2 mmol), base (1.7–2 mmol), DMF or DMPU solvent (0.5–0.6 mL). Yields are isolated yields. See the Supporting Information for details.

^b2,6-Diphenylpyridine oxide also isolated (20%).