From left: Y. H. Lee and Dr. B. Morandi (Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany)
New Synthetic Access to Ethers
Bill Morandi reports a new synthetic access to ethers through reductive cross-coupling.
Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me2SiHCl as both Reductant and Lewis Acid: Y. H. Lee, B. Morandi Synlett 2017, 28, DOI: 10.1055/s-0036-1590838
The textbook Williamson reaction is traditionally the method of choice for synthesizing dialkyl ethers using an SN2 reaction of an alkoxide nucleophile with an electrophilic alkyl halide. However, complex molecules and the presence of cross-reactive functions often require the use of milder reagents or more selective reaction conditions. A new highly versatile process for the synthesis of ethers, relying on the coupling between a ketone and an alcohol promoted by Me2SiHCl – which acts as both a Lewis acid and a reducing agent – was recently reported by the group of Dr. Bill Morandi from the Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr (Germany).
Dr. Morandi said: “This reaction is an extremely simple tool for the synthesis of ethers, which are essential structural motifs in many important applications.”