Table 3 Influences of bases and additives on the transition-metal-free cross-couplinga.

From: Transition-metal-free formal cross-coupling of aryl methyl sulfoxides and alcohols via nucleophilic activation of C-S bond

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Entry

Base

Additive

bAssay yield of 3a (%)

1

LiOtBu

—

0

2

NaOtBu

—

23

3

KOtBu

18-crown-6

5

4

NaOtBu

KF

63

5

LiOtBu

KF

27

  1. aReaction conditions: 1a (0.2 mmol), 2a (0.4 mmol), base (0.4 mmol) and additive (0.4 mmol) in DME (0.4 mL) under argon atmosphere at 110 °C for 12 h.
  2. bAssay yield determined by 1H NMR using 0.1 mmol (7.0 μL) CH2Br2 as internal standard.
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