Table 1.

Halogenation scope.^a

entry	arene	reagent base	product	yield
1		CCl4 tBuOLi		80%
2		CBr4 K3PO4		82%
3		CBr4 tBuOLi		91%
4		(BrCF2)2 tBuOLi		80%
5		CBr4 tBuOLi		56%
6b		CBr4 tBuOLi		30%
7	C6Cl5H	ICl tBuOLi		90%
8		CBr4 tBuOLi		55%
9		CBr4 tBuOLi		40%
10	C6F5H	I2 K3PO4		85%
11		I2 tBuOLi		98%
12		I2 tBuOLi		95%
13c		ICl tBuOLi		58%
14d		ICl tBuOLi		39%

^aSubstrate (1 equiv), base (2–4 equiv), halogenating reagent (1.5-4 equiv). Yields are isolated yields. See the Supporting Information for details.

^bm-Xylene solvent.

^c1,3,5-Trifluorobenzene (3 equiv), ICl (1 equiv).

^b1,3,5-Trifluorobenzene (1 equiv), ICl (4 equiv).