Beilstein J. Org. Chem.2019,15, 976–980, doi:10.3762/bjoc.15.95
catalyst-free novel and efficient methodology for the challenging synthesis of benzo-oxetes from 2'-hydroxyacetophenones mediated by sulfuryl fluoride (SO2F2) gas has been realized. The combination of 2'-hydroxyacetophenones and SO2F2 furnishes synthetically challenging benzo-oxetanes in moderate to
excellent yields. The highlight of this work is the design and synthesis of strained four-membered oxete rings.
Keywords: benzo-oxetes; 2'-hydroxyacetophenones; sulfuryl fluoride; Introduction
Oxetanes are versatile elements in drug discovery and synthesis [1][2], and represent important moieties in some
the reaction at 90 °C was essential for high efficiency of the transformation. Additional screening revealed that decreasing the amount of K2CO3 to 2.0 equiv or 1.0 equiv affected the cyclization process significantly to provide benzo-oxetes in 81% and 59% yield, respectively (Table 1, entries 11 and
PDF
Graphical Abstract
Scheme 1:
Synthetic pathways towards oxetanes and benzo-oxetes.