Table 1 Reaction optimizationa.

From: Direct transfer of tri- and di-fluoroethanol units enabled by radical activation of organosilicon reagents

View full size image

Entry

1a/7a/oxidant

Catalyst

Oxidant

t (h)

Yield (%)

1

1/1.2/0

Mn(OAc)3·2H2O (2 equiv.)

Without oxidant

18

68

2

1/1.5/2.5

Mn(OAc)3·2H2O (20 mol%)

TBPB

12

61

3b

1/1.5/2.5

Mn(OAc)3·2H2O (20 mol%)

TBPB

12

59

4c

1/1.5/2.5

Mn(OAc)3·2H2O (20 mol%)

TBPB

12

58

5d

1/1.5/2.5

Mn(OAc)3·2H2O (20 mol%)

TBPB

12

45

6

1/1.5/2.5

Mn(OAc)3·2H2O (20 mol%)

TBPB

18

62

7

1/2/2.5

Mn(OAc)2·4H2O (20 mol%)

TBPB

18

81

8

1/2/0

Mn(OAc)2·4H2O (20 mol%)

Without oxidant

18

0

9

1/2/2.5

Without catalyst

TBPB

18

0

10e

1/2/2.5

Mn(OAc)2·4H2O (20 mol%)

TBPB

18

0

  1. a1a was used as the reagent, otherwise noted; the yield of the product 8 was determined by 19F NMR with PhCF3 as an internal standard.
  2. b1b was used instead of 1a.
  3. c1c was used instead of 1a.
  4. d1d was used instead of 1a.
  5. eTrifluoroethanol was used instead of 1a.
Back to article page