A Ternary Catalytic System for the Room Temperature Suzuki-Miyaura Reaction in Water

Table 3

Screening of the best condition for the Suzuki reaction between 4-bromoacetophenone and phenylboronic acid.

Entry	Solvent	Catalyst	Pd : CD	Cyclodextrin	Time (h)	Conversion^a (%)
1	H2O	Na2PdCl4 1%	—	—	24	26
2	H2O : isopropyl alcohol (60% : 40%)	Na2PdCl4 1%	—	—	24	>99
3	H2O : isopropyl alcohol (80% : 20%)	Na2PdCl4 1%	—	—	24	>99
4	H2O : isopropyl alcohol (90% : 10%)	Na2PdCl4 1%	—	—	24	70
5	H2O : isopropyl alcohol (90% : 10%)	Na2PdCl4 1%	1 : 1	β-CD	24	68
6	H2O : isopropyl alcohol (90% : 10%)	Na2PdCl4 1%	1 : 10	β-CD	24	86
7	H2O : isopropyl alcohol (90% : 10%)	Na2PdCl4 1%	10 : 1	β-CD	24	59
8	H2O : isopropyl alcohol (90% : 10%)	Na2PdCl4 1%	1 : 10	HP-β-CD	24	>99
9	H2O : isopropyl alcohol (90% : 10%)	Na2PdCl4 1%	1 : 10	β-CD, sulfated sodium salt	24	86
10	H2O	Na2PdCl4 1%	1 : 10	HP-β-CD	24	>99
11	H2O	Na2PdCl4 0.5%	1 : 10	HP-β-CD	24	66
12	H2O	Na2PdCl4 0.5%	1 : 20	HP-β-CD	24	>99
13	H2O	Na2PdCl4 0.5%	1 : 20	HP-β-CD	2	57
14	H2O	Na2PdCl4 0.5%	1 : 20	HP-β-CD	4	58
15	H2O	Na2PdCl4 0.5%	1 : 20	HP-β-CD	6	89
16	H2O	Na2PdCl4 0.5%	1 :  20	HP-β-CD	7	93
17	H2O	Na2PdCl4 0.5%	1 : 20	HP-β-CD	8	>99
18	H2O	Pd/LDH 0.5%	1 : 20	HP-β-CD	8	>99
19	H2O	Pd/LDH 0.5%	—	—	8	93
20	H2O	HDL	—	HP-β-CD	8	—
21	H2O	Pd/LDH 0.1%	1 : 20	HP-β-CD	8	>99
22	H2O	Pd/LDH 0.01%	1 : 20	HP-β-CD	8	30
23	H2O	Pd/LDH 0.1%	1 : 20	HP-β-CD	3	60
24^b	H2O	Na2PdCl4 0.1%	1 : 20	HP-β-CD	8	45
25^b	H2O	Pd/LDH 0.1%	1 : 20	HP-β-CD	8	>99
26^b	H2O	Pd/LDH 0.1%	—	—	8	91

^aConversion of aryl halide into products measured by GC-MS.
^bReaction between iodobenzene and phenylboronic acid.