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. 2019 Nov 11;58(52):19014–19020. doi: 10.1002/anie.201911075

Table 1.

Influence of the amount of DABCO on the conversion of diazonium salt 2 a and the yield of sulfonimidate 3 a.[a] Inline graphic

Entry

DABCO [equiv]

Conversion of 2 a [%][b]

Yield of 3 a [%][b]

1

0

22

20

2

1.10

>95

60

3

0.55

88

43

4

0.10

26

15

5[c]

0.10

23

17

6[d]

0.55

>95

0

[a] Performed at room temperature for 20 min. [b] Determined by 19F qNMR with 3,3′‐bis(trifluoromethyl)benzophenone as internal standard. [c] Use of CaCO3 (1.10 equiv) in addition to DABCO. [d] Performed at 60 °C. DABCO=1,4‐diazabicyclo[2.2.2]octane, THF=tetrahydrofuran.