A series of alkenes and alkynes was subjected to reduction with hydrazine hydrate in ethanol in the presence of oxygen. An efficient method was developed for the reduction of C–C double bonds and C–C triple bonds with diimide, generated in situ from hydrazine hydrate by oxidation with oxygen. The reduction process proceeded for 24–48 hours with high chemoselectivity and excellent yields. This reduction procedure offers synthetic advantages over metal-catalyzed hydrogenation as well as other systems.
28 May 2015 in Beilstein Journal of Organic Chemistry
Various N-propargylpyrrole and indolecarboxylic acids were efficiently converted into 3,4-dihydropyrrolo- and indolo-oxazin-1-one derivatives by a gold(III)-catalyzed cyclization reaction. Some of the products underwent TFA-catalyzed double bond isomerization and some did not. Cyclization reactions in the presence of alcohol catalyzed by Au(I) resulted in the formation of hemiacetals after cascade reactions.