Table 2 Ethylene Insertion into Diphosphine 4aa and 4gb

From: A theory-driven synthesis of symmetric and unsymmetric 1,2-bis(diphenylphosphino)ethane analogues via radical difunctionalization of ethylene

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Entry

Compound

Photocatalyst

Light

Temp (°C)

C2H4 (atm)

3a (%)

4′a (%)

1

4aa

[Ir(ppy)2(dtbbpy)]PF6

Blue

rt

10

85

–

2

4aa

–

Blue

rt

10

74

12

3

4aa

–

White

rt

10

71

15

4

4aa

–

–

rt

10

50

24

5

4aa

–

–

50

10

40

26

6

4aa

–

–

rt

1

49

27

7

4gb

[Ir(ppy)2(dtbbpy)]PF6

Blue

rt

10

64

–

8

4gb

–

White

rt

10

80

–

9b

4gb

–

–

rt

10

35

15

  1. aYields were determined via 1H NMR analysis using 1,1,2,2-tetrachloroethane as the internal standard
  2. bDiphosphine 4gb was recovered in 34% yield together with its oxidized analog 4gb′ in 15% yield (total 49% recovery)
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