Table 1 Selected results of reaction optimizationa

From: Copper-catalyzed dehydrogenative γ-C(sp3)-H amination of saturated ketones for synthesis of polysubstituted anilines

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Entry

Additive (equiv.)

Solvent

Yield(%)b

1

–

PhCH3

80

2

o-nitro-benzoic acid (0.2)

PhCH3

85

3

o-nitro-benzoic acid (0.2)

o-DCB

67

4

o–nitro-benzoic acid (0.2)

CH3CN

63

5

benzoic acid (0.2)

PhCH3

53

6

acetic acid (0.2)

PhCH3

56

7

p-TsOH (0.05)

PhCH3

87

8

p-TsOH (0.1)

PhCH3

96

9

p-TsOH•H2O (0.1)

PhCH3

83

10

p-TsOH (0.2)

PhCH3

91

11c

p-TsOH•H2O (0.08)

PhCH3

30

12c

p-TsOH (0.1)

PhCH3

33

13c

p-TsOH (0.2)

PhCH3

21

14c

–

PhCH3

trace

  1. aReaction conditions: 1a (2 equiv.), 2a (0.4 mmol), 3a (1.5 equiv.), Cu(OAc)2 (10 mol%), bpy (10 mol%), TEMPO (3 equiv.), additive, solvent (1.5 mL), N2, 120 °C for 48 h
  2. bIsolated yields
  3. cWithout Cu(OAc)2/bpy
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