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

Table 2

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

Entry	Substrate 1	Substrate 2	Product	Conversion [%]/isolated yield [%]
1		2a		75/47
2		2a		47
3		2a		65
4		2a		93/55
5		2a		69/44
6		2a		72/45.3
7		2a		65/36
8		2a		21
9		2a		69
10		2a		44
11		2a		62/37.5
12		2a		22
13		2a		37
14		2a		54/32
15				32 (o : m : p = 3.1 : 1.5 : 1)
16				60 (o : m : p = 2.2 : 1 : 1.5)
17				70/44
18				12
19				85

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.).