Table 2: Direct cross-coupling of benzene with different aryl halides (see Scheme 4).

EntrySubstrate 1Substrate 2ProductConversion [%]/isolated yield [%]

12a75/47
22a47
32a65
42a93/55
52a69/44
62a72/45.3
72a65/36
82a21
92a69
102a44
112a62/37.5
122a22
132a37
142a54/32
1532 (o : m : p = 3.1 : 1.5 : 1)
1660 (o : m : p = 2.2 : 1 : 1.5)
1770/44
1812
1985

General reaction conditions: 4-chlorotoluene (0.1 mmol, 1 equiv.), benzene (11.24 mmol, 112.4 equiv.), room temperature (air cooling), N2 atmosphere (balloon pressure), and UV light irradiation (254 nm, 10 mW·cm−2, 24 h). Isolated yield by silica gel column chromatography. Ratios of the regioisomers were determined by NMR. Aniline (11.0 mmol, 110 equiv.). Cyclohexylamine (8.77 mmol, 87.7 equiv.). Acetonitrile (1 mL), p-methoxyaniline (1 mmol, 10 equiv.).