Palladium-Catalyzed Intermolecular Dehydrogenative Carboamination of Alkenes with Amines and N-Substituted Isatin.

The first intermolecular dehydrogenative carboamination of alkenes with aromatic amines and N-substituted isatin has been developed using palladium as a catalyst. This multicomponent reaction is a valuable synthetic tool for difunctionalization of the alkene with retention of the C-C double bond. This reaction has two very distinguishing features: (1) the formation of the C-N and C-C bonds with retention of the double bond and (2) high regioselectivity. Thus, this strategy has opened up a new area in chemistry.

Betaine mediated synthesis of annulated dihydrofurans from oxobis(methylthio)ketene acetals and N-butyl-N'-methyl ethane-1,2-diamine as precursors via NHC elimination.

First in situ generation of a betaine intermediate has been developed using two new precursors oxobis(methylthio)ketene acetals and N-butyl-N'-methyl ethane-1,2-diamine for the synthesis of annulated dihydrofurans. This protocol adds a new dimension for the formation of annulated dihydrofurans through a series of selective consecutive formation of C-C and C-O bonds after reacting with enone rings. This in situ generated betaine intermediate corresponds to deoxy-Breslow intermediates in the reaction via elimination of NHC.