Table 1 Variation of reaction parameters

From: Regio-, stereo-, and enantioselective ipso- and migratory defluorinative olefin cross-coupling to access highly functionalized monofluoroalkenes

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Entry

Deviation from standard conditions

Yield of 3a (%)a

ee (%)

1

none

85 (83)

92

2

NiBr2∙dme instead of NiI2·xH2O

33

88

3

Ni(cod)2 instead of NiI2·xH2O

trace

4

L1aa instead of L1a

34

69

5

L1ba instead of L1a

58

5

6

L2a instead of L1a

26

0

7

DMMS instead of DEMS

66

92

8

w/o KI

72

93

9

NaI instead of KI

71

91

10

w/o TBAF

7

6

11

Na3PO4 instead of TBAF

76

92

12

NaF (1 equiv) instead of TBAF

82

91

13

THF instead of DMA

40

77

14

0 °C

53

94

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  1. aYields were determined by gas chromatography (GC) using n-dodecane as the internal standard, the yield within parentheses is the isolated yield and is an average of two runs (0.20 mmol scale).
  2. Enantioselectivities were determined by HPLC analysis.
  3. PMP para-methoxy phenyl, DEMS diethoxymethylsilane, DMMS dimethoxymethylsilane, DMA N,N′-dimethylacetamide, TBAF tetrabutylammonium fluoride.