Table 1 Optimization of reaction conditionsa

From: Photo-induced hydroxypentafluorosulfanylation of alkenes with SF5Cl and oxygen gas and their further derivatization

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Entry

Deviation from the standard conditions

Yield [%]b

1

None

89

2

No 1-hexene

52

3

No H2O

69

4

No O2

N. D.

5

CHCl3 instead of DCM

60

6

CCl4 instead of DCM

54

7

THF instead of DCM

<5

8

Acetonitrile instead of DCM

<5

9

427 nm LEDs instead of 365 nm LEDs

61

10

390 nm LEDs instead of 365 nm LEDs

64

11

1 equiv. SF5Cl instead of 2 equiv.

57

12

DCM (0.2 M) instead of DCM (0.1 M)

65

  1. N.D. denotes not detected.
  2. aReaction conditions (unless otherwise specified): 1 (0.05 mmol), 2 (0.1 mmol, ~0.3 M in n-hexane), H2O (0.05 mmol), O2 (0.09 mmol), 1-hexene (0.01 mmol), DCM (0.5 mL), 365 nm LEDs, r.t., 4 h, N2 atmosphere.
  3. bYields were determined based on the isolated products.