Rhodium-Catalyzed C-O Bond Alkynylation of Aryl Carbamates with Propargyl Alcohols.

The rhodium-catalyzed alkynylation of aryl carbamates with propargyl alcohols is described. This methodology can provide aryl acetylenes from aryl carbamates via C-O bond activation. The use of propargyl alcohols as alkynylating agents allows the use of a variety of functional groups that are incompatible with organometallic nucleophiles. This reaction also serves to broaden the utility of a carbamate moiety as a convertible ortho directing group.