Table 2 Optimization of the Fe-catalyzed hydrofunctionalization with commercial tosyl chloride and tosyl azide as the atom or group transfer reagents

From: Iron-catalyzed radical Markovnikov hydrohalogenation and hydroazidation of alkenes

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Entrya

Fe–H source

Radical trap

Conversion

Yield

1

Fe(dpm)3, 4 (2.0 eq.)

6a (1.5 eq.)

76% (1b)

74% (7b)

2

Fe(dpm)3, PhSiH3 (2.0 eq.)

6a (1.5 eq.)

64% (1b)

62% (7b)

3

Fe(acac)3, 4 (2.0 eq.)

6a (1.5 eq.)

23% (1b)

23% (7b)

4

Fe(dpm)3, 4 (2.0 eq.)

6a (3.0 eq.)

77% (1b)

77% (7b)

5b

Fe(dpm)3, 4 (2.0 eq.)

6a (1.5 eq.)

57% (1b)

50% (7b)

6

Fe(dpm)3, 4 (2.0 eq.)

6a (1.5 eq.)

75% (1a)

48% (7a)

7

Fe(dpm)3, 4 (2.0 eq.)

6a (1.1 eq.)

79% (1a)

61% (7a)

8c

Fe(dpm)3, 4 (3.0 eq.)

6a (1.1 eq.)

90% (1a)

82% (7a)

9d

Fe(acac)3, PhSiH3 (4.0 eq.)

6a (1.5 eq.)

81% (1a)

80% (7a)

10e

Fe(acac)3, PhSiH3 (4.0 eq.)

6a (1.5 eq.)

80% (1a)

75% (7a)

11

Fe(dpm)3, 4 (2.0 eq.)

6b (1.5 eq.)

76% (1a)

62% (8a)

12

Fe(dpm)3, 4 (2.0 eq.)

6b (1.5 eq.)

84% (1b)

71% (8b)

  1. aReactions were carried out on a 0.1 mmol scale. The reactions were stirred until no further conversion was observed by GC analysis. Conversion and yield were determined by GC analysis using dodecane as an internal standard.
  2. bConnected to air by needle.
  3. cStirred for 72 h.
  4. dStirred for 194 h.
  5. eAt 40 °C for 48 h.
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