title: A mild C-O bond formation catalyzed by a rhenium-oxo complex.
abstract: A mild method for the regioselective synthesis of propargyl ethers by the coupling of propargyl alcohols with a range of other alcohols is described. The method employs an air- and moisture-tolerant rhenium-oxo complex ((dppm)ReOCl3) as a catalyst for the formation of sp3-carbon-oxygen bonds without the need for prior activation of the propargyl alcohol or deprotonation of the alcohol nucleophile. A broad range of functional groups is tolerated, including aryl halides, olefins, esters, and acid-labile functional groups such as acetals. Furthermore, displacement of the alcohol occurs preferentially even in the presence of other electrophiles such as primary alkyl halides and conjugated esters.
authors.affiliation: Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley 94720, USA.
authors.forename: Benjamin D
authors.initials: BD
authors.lastname: Sherry
authors.forename: Alexander T
authors.initials: AT
authors.lastname: Radosevich
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste