Table 1 Exploration and optimization of reaction conditions

From: Photocatalyst-free photochemical deuteration via H/D exchange with D2O

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Entry

Variation of standard conditions

Yield (%)a

D ratio (%)b

1

None

92 (79c)

94

2

420 nm instead of 380 nm

95

85

3

thiol II instead of thiol I

91

57

4

thiol III instead of thiol I

90

24

5

thiol I (30 mol%) instead of thiol I (5 mol%)

96

80

6

thiol I (1 mol%) instead of thiol I (5 mol%)

87

87

7

MeCN instead of EtOAc

96

72

8

CHCl3 instead of EtOAc

76

19

9

EtOAc (0.1 M) instead EtOAc (0.2 M)

89

93

10

Without thiol I

84

8

11

Without light

96

<5

  1. aYield was determined by 1H NMR.
  2. bD ratio was determined by 1H NMR.
  3. cIsolated yield.