Table 1 Optimization of gold-catalyzed oxo-arylfluorinationa

From: Gold-catalyzed four-component multifunctionalization of alkynes

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Entry

Variation of standard conditions

Yield(%)b

1

None

70

2

Ph3PAuCl (10 mol%)

58

3

dppm(AuCl)2 (5 mol%)

38

4

(4-CF3Ph)3PAuTFA (10 mol%)

53

5

(4-CF3Ph)3PAuOTs (10 mol%)

50

6

without (4-CF3Ph)3PAuCl

N.D.

7

H2O (5.0 equiv)

61

8

without H2O

49

9

NFSI instead of Selectfluor

N.D.

  1. aStandard reaction conditions: 1a (0.1 mmol), 2a (0.3 mmol), (4-CF3Ph)3PAuCl (10 mol%), Selectflour (4.0 equiv.), H2O (2.0 equiv.), MeCN (2.0 mL), 50 °C, air, 12 h.
  2. bIsolated yields. dppm bis(diphenylphosphino)methane, Selectfluor 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), NFSI N-fluorobenzenesulfonimide.
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