Journal of Synthetic organic Chemistry SUPPORTING INFORMATIONSYNTHESIS

Thieme

Supporting Information

NHC-Pd(II)-Im (NHC = N-heterocyclic carbene, Im =

1-methylimidazole) complex catalyzed Suzuki-Miyaura

coupling reaction of aryl chlorides in water

Xia-Xia Zhou and Li-Xiong Shao*

College of Chemistry and Materials Engineering, Wenzhou University, Chashan

University Town, Wenzhou, Zhejiang Province 325035, People’s Republic of China

shaolix@wzu.edu.cn

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Entrya Time Yield(%)b

1

2

3

4

5

6

7

8

9

2b (4-OMe) 12 h 89

2d (4-NO2) 12 h 53

2e (3-Me)

2j

2k

2c (3-MeO)

2f (2-Me)

2i (2,6-Me2C6H3)

12 h

12 h

12 h

24 h

24 h

24 h

24 h

50

99

97

N Cl

N

Cl

98

40

2h (4-CHO) trace

trace

10 2lS Cl

24 h 34

a All reactions were carried out using 2 (0.5 mmol), 3 (0.6

mmol), 1 (2.0 mol%), NaOH (2.0 equiv), H2O (2.0 mL) at 80 oC

for the listed time. b Isolated yields.

2 (R1)

H2O, 80 oC, 12-24 h

Cl B(OH)2 complex 1 (2.0 mol%)

+

2 3

NaOH (2.0 equiv)

R1 R2

R1

R2

4

Table SI-1 Complex 1 Catalyzed Coupling Reactions of Aryl Chlorides 2 with Boronic Acids 3 Using NaOH as the Base.

3 (R2)

3d (2-Me)

3b (H)

3a (4-MeO)

3b

3a

3b

3d

3a

3a

3a

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