Table 1 Reaction optimization and control experiments.

From: Arene dearomatization through a catalytic N-centered radical cascade reaction

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Entry

Photocatalyst

Solvent

Yield (%)

1

A

PhCF3 (0.2 M)

48

2

B

PhCF3 (0.2 M)

32

3

C

PhCF3 (0.2 M)

7

4

A

PhCF3 (0.05 M)

67

5

A

DMF (0.05 M)

50

6

A

CH2Cl2 (0.05 M)

47

7

A

1,2-DCE (0.05 M)

65

8

A

t-BuOH (0.05 M)

73

9

A

PhCF3/t-BuOH (0.05 M)

83 (75)a

Variation from best conditions (Entry 9)

10

No blue LEDs

0

11

No photocatalyst

0

12

No NBu4OP(O)(OBu)2

0

  1. See Supplementary Tables 1 and 2 for complete optimization details. Reactions were run on 0.1 mmol scale, and yields are determined by 19F-NMR analysis relative to 1,3,5-trifluorobenzene (1 equiv.) as an internal standard.
  2. aIsolated yield of 2a on 0.2 mmol scale.