Synthesis of Dialkyl Ethers from Organotrifluoroborates and Acetals
Journal of the American Chemical Society2009Vol. 131(50), pp. 18057–18059
Citations Over TimeTop 10% of 2009 papers
Abstract
The formation of ethers by C-O bond formation under harsh basic or acidic conditions is an entrenched synthetic disconnection in organic chemistry. We report a strategic alternative that involves the BF(3).OEt(2)-promoted coupling of stable, easily prepared acetals with widely available potassium aryl-, alkenyl-, and alkynyltrifluoroborates. This fast, operationally simple process offers straightforward access to dialkyl ethers, many of which would be difficult to prepare using classical methods. The use of MOM-protected alcohols and acetal-protected aldehydes enables ether formation without recourse to protecting-group manipulations or strong bases.
Related Papers
- → Synthesis and Evaluation of 1-Arylsulfonyl-3-piperazinone Derivatives as Factor Xa Inhibitors VI. A Series of New Derivatives Containing N,S- and N,SO2-Spiro Acetal Scaffolds(2007)10 cited
- → 2-tert-Butoxy-3-phenylcyclopropanone acetal, a stable precursor of lithiated 2-phenylcyclopropenone acetal(2007)2 cited
- → A synthesis of the acetal of dl‐pelletierine or β‐(2‐piperidyl)‐propionaldehyde acetal.(1941)19 cited
- → Synthetic Studies Starting from β-Cyanopropionaldehyde. I. The Synthesis of Adipic Dialdehyde(1964)6 cited
- Progress in surfactants with acetal group in molecular structure(2003)