Two birds with one stone: one-pot simultaneous synthesis of 2,2,2-trifluoroethylphenanthridines and benzochromenones featuring the utilization of the byproduct of Togni's reagent

Abstract

A one-pot simultaneous synthesis of 2,2,2-trifluoroethylphenanthridines and benzochromenones featuring the utilization of the byproduct of Togni's reagent is presented.

Synthesis of Esterified/Fused Isocoumarins via Rh-Catalyzed C—H Activation/Transannulative Coupling/Annulation of Phthalic Anhydrides with Cyclic 2-Diazo-1,3-diketones and Methanol

“…[8] Recently, an impressive transition metal-free α-arylation/ring annulation and Rh-catalyzed direct C-H activation of ylides with diazo compounds have been developed for efficient access to fused isocoumarins. [9][10][11][12][13] Despite these approaches being efficient and reliable, developing more streamlined and practical methods from the available reagents for the synthesis of diversified isocoumarins is highly desirable.…”

Enantioselective Synthesis of Fused Isocoumarins via Palladium-Catalyzed Annulation of Alkyne-Tethered Malononitriles

“…Efficient access to fused isocoumarins via Rh-catalyzed direct C–H activation of benzoic acid derivatives and coupling with carbene precursors (e.g., diazo compounds, iodonium ylides, etc.) was also developed (Scheme a­(i)). − Even though useful, these approaches are all limited to nonenantioselective processes.…”

Selective Synthesis of 2-Indolyl-3-oxoindolines or 2-(2-Aminophenyl)quinolines through Cu(II)- or Bi(III)-Catalyzed Tunable Dimerizations of 2-Alkynylanilines

“…In the past several years, we have developed some methods for the synthesis of biologically interesting heterocyclic compounds . In this regard, we recently disclosed the synthesis of indolo­[3,2- c ]­quinolines and 3-(2-aminophenyl)­quinolines via [RhCp*Cl 2 ] 2 -catalyzed dimerization of 2-alkynylanilines under aerobic/anaerobic conditions (Schemes a and b) .…”

“…When this reaction was run under an inert atmosphere (N 2 ) instead of air, 4a , the 4-alkyl counterpart of 3a , was selectively obtained in 64% yield (entry 22). Interestingly, 4a has a different substitution pattern compared with the quinoline product obtained from [RhCp*Cl 2 ] 2 -catalyzed dimerization of the same substrate (Scheme e vs b), indicating that two different dimerization pathways must have been involved.…”