Table 1 Screening of reaction conditions.a

From: Carbon–nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes

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Entry

Variation from ‘standard conditions

Yield (%)b

1

None

80 (61)c

2

w/o FeBr2

trace

3

FeCl2 instead of FeBr2

71

4

Fe(OTf)2 instead of FeBr2

75

5

Fe(OAc)2 instead of FeBr2

32

6

Fe(acac)3 instead of FeBr2

10

7

Cu(OTf)2 instead of FeBr2

<10

8

[[CH3(CH2)6CO2]2Rh]2 instead of FeBr2

34

9

TMOPP-Co instead of FeBr2

trace

10

Ru3(CO)13 instead of FeBr2

<10

11

w/o Cy3PO

70

12

In toluene

75

13

In THF

70

14

10 mol% FeBr2 and 15 mol% Cy3PO instead

61

  1. aUnless otherwise specified, all reactions were carried out using 1a (0.1 mmol), NBS (0.18 mmol), N(nBu4)N3 (0.3 mmol), (PhO)2POOH (0.075 mmol), FeBr2 (0.015 mmol), and Cy3PO (0.02 mmol) in PhCl (1.0 mL) at 100 °C for 36 h.
  2. bIsolated yields after chromatography.
  3. cScale-up reaction by using 1.0 mmol of 1a.