Table 1.

Cross-coupling of a range of boronic acids with 4-chloroacetophenone.

Entrya	ArB(OH)2	Base	Conversion to product (%)	Isolated Yield (%)
1	PhB(OH)2	K3PO4	85	70
2	PhB(OH)2	CsF	96	85
3	4-F-C6H4B(OH)2	K3PO4	88	72
4	4-F-C6H4B(OH)2	CsF b	42	23
5	4-F-C6H4B(OH)2	CsF c	49	N.D.
6	4-F-C6H4B(OH)2	CsF	>98	98
7	3-F-C6H4B(OH)2	K3PO4	87	73
8	3-F-C6H4B(OH)2	CsF	92	69
9	2-F-C6H4B(OH)2	K3PO4	82	53
10	2-F-C6H4B(OH)2	CsF	81	64
11	2-MeO-C6H4B(OH)2	CsF	92	80
12	2-MeO-C6H4B(OH)2	CsFd	>98	ND
13	4-MeO-C6H4B(OH)2	CsF	82	69
14	3-Napthyl	CsF	64	61
15	2,3,6-F3C6H2B(OH)2	CsF	<5	N.D.
16e	2,3,6-F3C6H2B(OH)2	CsF	<5	N.D.

a: Reactions performed using 1% catalyst 2, 0.5 mmol of 4-chloro-acetophenone under the conditions described in Scheme 2, unless otherwise stated. Conversion to product refers to the NMR yield of the reactions. Yield refers to isolated yield of pure material after column chromatography, or in the case of entries 3–10, recystallisation. N. D. = not determined. b: DMF used as solvent. c: 1.0 mmol of aryl chloride, 1.5 mmol of boronic acid; 3 mmol of base. d: Reaction time extended to 15 minutes. e: 3-bromoacetophenone used as coupling partner.