Table 1 Reaction screening of C-H activation for TFMAQ-7Ph 1 catalyzed by palladium-ligand systems.

From: Selective synthesis of substituted amino-quinoline derivatives by C-H activation and fluorescence evaluation of their lipophilicity-responsive properties

View full size image

Entrya

1

2

3

4

5

6

[Pd]

Pd(OAc)2

Pd(OAc)2

Pd(OAc)2

Pd(OAc)2

Pd(OAc)2

Pd(OAc)2

Ligand

DPPF

t-Bu3P

DPPE

XPhos

Xantphos

JohnPhos

2 yieldb (%)

Tracec

77

n.d.

63

56

86

3 yieldb (%)

30

n.d.d

Trace

Trace

Trace

Trace

Entry

7

8

9

10

11

12

[Pd]

Pd(OAc)2

Pd(OAc)2

Pd(DPPF)Cl2

Pd(PPh3)2Cl2

Pd(PCy3)2Cl2

Pd(CH3CN)2Cl2

Ligand

DtBPF

QPhos

2 yield (%)

73

81

Trace

Trace

12

n.d.

3 yield (%)

Trace

Trace

88

61

40

n.d.

  1. aThe reaction was performed with 0.07 mmol of 1, 3 eq of PhBr, 18 mol% of palladium [Pd], 30 mol% of phosphine ligand, and 3 eq of t-BuOK in 1 mL of toluene at 110 °C for 3 h. bIsolated yield. cDetected only on TLC. dNot detected. DPPE = Ethylenebis(diphenylphosphine). XPhos = 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl. Xantphos = 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene. JohnPhos = 2-(Di-tert-butylphosphino)biphenyl. DtBPF = Bis[(di-tert-butylphosphino)cyclopentadienyl]iron. QPhos = 1,2,3,4,5-Pentaphenyl-1′-(di-tert-butylphosphino)ferrocene.
Back to article page