Optimization of Suzuki–Miyaura reaction^a.

Entry	HCP-Pd	Solvent	Base	Yieldb (%)
1	1.0	EtOH	NaOH	84
2	1.0	DMSO	NaOH	55
3	1.0	DMF	NaOH	79
4	1.0	Toluene	NaOH	39
5	1.0	THF	NaOH	NRc
6	1.0	CH3CN	NaOH	Trace
7	1.0	H2O	NaOH	18
8	1.0	EtOH/H2O (4 : 1)	NaOH	99
9	1.0	EtOH/H2O (2 : 1)	NaOH	92
10	1.0	EtOH/H2O (1 : 1)	NaOH	89
11	1.0	EtOH/H2O (1 : 4)	NaOH	51
12	1.0	EtOH/H2O (4 : 1)	K2CO3	96
13	1.0	EtOH/H2O (4 : 1)	K3PO4	98
14	1.0	EtOH/H2O (4 : 1)	Cs2CO3	95
15	1.0	EtOH/H2O (4 : 1)	Na2CO3	69
16	1.0	EtOH/H2O (4 : 1)	Et3N	Trace
17	0.5	EtOH/H2O (4 : 1)	NaOH	76

^aReaction conditions: 1a (2.5 mmol), 2a (3.5 mmol), HCPs-Pd (1.0 mg, 1.5 × 10⁻⁴ mmol), 60 °C, 1.0 h.

^bIsolated yields.

^cNo reaction.