From Aniline to Aryl Ether: A Facile, Efficient and Versatile Synthetic Protocol Employing Mild Conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2018)
Abstract
We have developed a simple and direct method for the synthesis of aryl ethers by reacting alcohols/phenols (ROH) with aryl ammonium salts (ArNMe3+), which are readily prepared from anilines (ArNR2, R=H or Me). This reaction proceeds smoothly and rapidly (within a few hours) at room temperature in the presence of a commercially available base, such as (KOBu)-Bu-t or KHMDS, and has a broad substrate scope with respect to both ROH and ArNR2. It is scalable and compatible with a wide range of functional groups.
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Key words
amines,C-N cleavage,C-O formation,ethers,late-stage functionalization
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