Decarboxylative cascade cyclization of α-keto acids with 2-cyano-3-arylaniline-derived acrylamides.

An oxidative decarboxylative cascade cyclization of α-keto acids with 2-cyano-3-arylaniline-derived acrylamides was developed. This cascade reaction exhibits a broad substrate scope, and provides an efficient access to carbonyl-containing pyrido[4,3,2-gh]phenanthridines. A possible mechanism is proposed.

Copper-Catalyzed Decarboxylative Oxyalkylation of Alkynyl Carboxylic Acids: Synthesis of γ-Diketones and γ-Ketonitriles.

A novel copper-catalyzed decarboxylative oxyalkylation of alkynyl carboxylic acids with ketones and alkylnitriles via direct C(sp3)-H bond functionalization to construct new C-C bonds and C-O double bonds was developed. This transformation is featured by wide functional group compatibility and the use of readily available reagents, thus affording a general approach to γ-diketones and γ-ketonitriles. A possible mechanism is proposed.

Metal-Free Radical [2 + 2 + 1] Cyclization of ortho-Cyanoarylacrylamides with Alkyl Nitriles: Synthesis of Pyrrolo[3,2- c]quinolines.

A novel radical [2 + 2 + 1] cyclization of ortho-cyanoarylacrylamides with dual α-C-H bonds in alkyl nitriles has been developed. The reaction provides new facile and straightforward access to cyano-substituted pyrrolo[3,2- c]quinolines, which are important nitrogen-containing polyheterocycles. A possible mechanism for the transformation is proposed.

Copper-Catalyzed Decarboxylative Disulfonylation of Alkynyl Carboxylic Acids with Sulfinic Acids.

A copper-catalyzed decarboxylative disulfonylation of alkynyl carboxylic acids with sulfinic acids in aqueous solution has been developed. The reaction provides a straightforward and practical access to (E)-1,2-disulfonylethenes, which are important building blocks in synthetic organic chemistry, and exhibits a good functional group tolerance and excellent stereoselectivity. A possible mechanism for the transformation is proposed.