Table 4.

The coupling reactions of aryl halides with various arylboronic acids^a.

Entry	Aryl halide 1	Arylboronic acid 2	Time (min)	Yieldb (%)	Product 3
1	C6H5I	C6H5B(OH)2	20	85	3a
2	4-NO2-C6H4I	C6H5B(OH)2	10	95	3b
3	4-Cl-C6H4I	C6H5B(OH)2	10	92	3c
4	4-Me-C6H4I	C6H5B(OH)2	15	85	3d
5	4-MeO-C6H4I	C6H5B(OH)2	15	93	3e
6	4-MeO-C6H4I	4-MeO-C6H4B(OH)2	18	65	3f
7	4-MeO-C6H4I	4-Me-C6H4B(OH)2	15	95	3g
8	4-MeO-C6H4I	4-Cl-C6H4B(OH)2	15	93	3h
9	4-MeO-C6H4I	4-F-C6H4B(OH)2	15	94	3i
10	4-MeO-C6H4I	4-CHO-C6H4B(OH)2	15	96	3j
11	4-NO2-C6H4I	4-MeO-C6H4B(OH)2	15	98	3k
12	4-NO2-C6H4I	4-Me-C6H4B(OH)2	8	68	3l
13	4-NO2C6H4I	4-Cl-C6H4B(OH)2	15	86	3m
14	4-NO2-C6H4I	4-F-C6H4B(OH)2	15	96	3n
15	4-NO2-C6H4I	4-CHO-C6H4B(OH)2	10	91	3o
16	C6H5Br	C6H5B(OH)2	15	63	3a
17	4-Me-C6H4Br	C6H5B(OH)2	30	60	3d
18	4-MeO-C6H4Br	C6H5B(OH)2	25	75	3e
19	4-NO2-C6H4Br	C6H5B(OH)2	15	96	3b
20	3-NO2-C6H4Br	C6H5B(OH)2	10	93	3p
21	4-Br-C6H5Br	C6H5B(OH)2	50	48	3q
22	4-MeO2C-C6H4Br	C6H5B(OH)2	20	98	3r
23	4-NO2-C6H4Cl	C6H5B(OH)2	12 h	23	3b

^aReaction conditions: aryl halide (1.0 mmol), arylboronic acid (1.2 mmol), K₂CO₃ (2.0 mmol), Cell–OPPh₂–Pd⁰ (0.015 g, 0.005 mmol of Pd), and 5.0 cm³ 95% ethanol heating under reflux in air. ^bIsolated yield based on aryl halide.