Double-Oxidative Dehydrogenative [4+2]-Cyclization/Dehydrogenation/Oxygenation Tandem Reaction of N-Arylglycine Derivatives with Cumenes

Abstract

Double-oxidative dehydrogenative (DOD) cyclization is one of the most straightforward strategies for the synthesis of cyclic compounds. A novel approach to substituted 3,4-dihydroquinoline-3-one derivatives via a Cu­(II)/DDQ/O2 system-catalyzed DOD [4+2]-cyclization/dehydrogenation/oxygenation cascade reaction of N-arylglycine derivatives, cumenes, and O2 has been developed.

Asymmetric Double Oxidative [3 + 2] Cycloaddition for the Synthesis of CF3-Containing Spiro[pyrrolidin-3,2′-oxindole]

“…Typical cycloadditions involve two or more unsaturated molecules or parts of the same molecule . The oxidative functionalization of C–H bonds for the formation of C–C bonds has become an important field within the requirements of green chemistry, which also inspired the development of new [ n + 2]-cycloadditions for the synthesis of structurally complex molecules from easily available saturated precursors. − Recently, double oxidative [4 + 2] cycloadditions have been developed for the synthesis of quinoline derivatives by the Liu and Huo groups, respectively, and cyclohexene-derived diketones by Zhou and co-workers, which use neither [4π] nor [2π] motifs as the starting materials. These transformations feature a high degree of step economy and no intermediate purification steps.…”