Solid phase synthesis of functionalized biaryl ethers: Versatile scaffolds for combinatorial chemistry

Jac C.H.M. Wijkmans, Anthony D. Baxter, Andrew J. Culshaw
Oxford Diversity, A Division of Oxford Asymmetry Ltd., 57 Milton Park, Abingdon, Oxon OX14 4RX, U.K.

Abstract
4-Fluoro-3-nitrobenzoic acid attached to a solid support was shown to react under mild conditions with a wide range of functionalized phenols to yield, after cleavage, the corresponding biaryl ethers in excellent purity. In a similar fashion, biaryl thioethers could be obtained. Further elaboration of immobilized biaryl ethers demonstrates the potential for combinatorial library generation.

Keywords
aromatic nucleophilic substitution, biaryl ethers, biaryl thioethers, scaffolds