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. 2019 Jan 29;10(11):3237–3241. doi: 10.1039/c8sc05096a

Table 1. Optimisation of the Cu-catalysed cross-coupling of aryl boronic acid 6a with ethyl bromofluoroacetate towards ester 7a and the corresponding carboxylic acid 8a a .

Inline graphic
Entry Solvent Cu-source Ligand Product Yield b
1 c Dioxane (0.2 M) CuI L1 7a 7%
2 c Dioxane (0.2 M) CuI L2 7a 58%
3 Toluene (0.2 M) CuI L3 7a 63%
4 d Toluene (0.4 M) CuI L3 7a 82% e
5 d Toluene (0.4 M) CuI L3 8a 75% e , f
6 d Toluene (0.4 M) CuI 7a 0%
7 d Toluene (0.4 M) 7a 0%
8 d Toluene (0.4 M) CuCl2 L2 7a 0%
9 d DMF or DMSO (0.2 M) CuI L3 7a 0%

aScreening reactions performed on 0.1 mmol scale.

bYield determined by 19F-NMR using α,α,α-trifluorotoluene as internal standard.

c2 equiv. of 6a and 1 equiv. of ethyl bromofluoroacetate.

d1 equiv. of 6a, and 2 equiv. of ethyl bromofluoroacetate.

eYield of isolated product.

fOne-pot procedure towards 8a.