ABSTRACT
Herein, a method to access 3-trifluoromethyl-1,4-benzoxazines from CF3-imidoyl sulfoxonium ylides and 2-bromophenols has been demonstrated. This synthetic protocol proceeds via a one-pot two-step sequence that includes the lithium-bromide-promoted O-H insertion of sulfoxonium ylides and annulation, and has the merits of broad substrate scope, excellent functional tolerance and operational simplicity, which provides an alternative means of obtaining CF3-substituted heterocycles.
Subject(s)
Oxazines , Phenols , Catalysis , Molecular StructureABSTRACT
Herein, a new strategy for the direct synthesis of functionalized pyrroles from ß-amino alcohols and ynones via ruthenium-catalyzed acceptorless dehydrogenative coupling has been demonstrated. This developed methodology proceeds in an atom- and step-economic fashion together with the merits of broad substrate scope, operational simplicity, and water and hydrogen gas as the sole by-products, which provides an alternative and sustainable way to access functionalized pyrroles. Further, this method was applied to the rapid synthesis of the COX-1/COX-2 inhibitor and boron dipyrromethene derivative successfully.