Synthesis of dialkyl ethers from organotrifluoroborates and acetals.
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.
Mitchell
T Andrew
TA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
Bode
Jeffrey W
JW
D000080:Acetals / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure
D000080:Acetals; D001881:Borates; D004987:Ethers; D006845:Hydrocarbons, Fluorinated