A breakthrough in the synthesis of diaryl ethers has been achieved as shown in Equation (1). The coupling of phenols with aryl boronic acids in the presence of copper(II) acetate and a base proceeds under very mild conditions (room temperature) as described simultaneously by Evans et al. and Chan et al. Examples: R(1)=2-Cl, 2-I, 2-OMe, 4-tBu, 4-CH(2)CH(NHCOOtBu)CO(2)Me, 3,5-tBu(2); R(2)=2-Me, 3-OMe, 3-NO(2), 4-H, 4-F, 4-OMe.
[reaction: see text] Kinetic resolution of a fluorous ester rac-1 with Candida antarctica B lipase provided a mixture of enantioenriched alcohol (R)-2 and fluorous ester (S)-1. The mixture was subjected to a fluorous triphasic reaction to give both enantiomers of 1-(2-naphthyl)ethanol 2 in high ee without chromatographic separation or fluorous-organic liquid-liquid extractive purification.
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