Photoinduced C-C Cross-Coupling of Aryl Chlorides and Inert Arenes

Table 5

Direct trifluoromethylation of trifluoromethanesulfonyl chloride with benzene derivatives (see Scheme 6).

Entry	R	Product	Conversion (%)
1	H		20
2	I		15 (m : p = 1 : 1)
3	Me		40 (o : m : p = 3 : 6 : 1)
4	OMe		30 (o : m : p = 2.3 : 1 : 1)
5	CN		21

General reaction conditions: trifluoromethanesulfonyl chloride (0.1 mmol, 1 equiv.), benzene (11.24 mmol, 112.4 equiv.), iodobenzene (8.93 mmol, 89.3 equiv.), toluene (9.43 mmol, 94.3 equiv.), anisole (9.2 mmol, 92 equiv.), benzonitrile (9.79 mmol, 97.9 equiv.), room temperature (air cooling), N₂ atmosphere (balloon pressure), and UV light irradiation (254 nm, 10 mW·cm⁻², 24 h); conversions were determined by ¹⁹F NMR with benzotrifluoride as an internal standard.