Sungkyunkwan University · Chemistry
Professor Neeraj Kumar Mishra's research lab specializes in transition metal-catalyzed C–H functionalization, with a strong focus on rhodium(III)-catalyzed transformations for the selective and efficient construction of complex nitrogen-containing heterocycles. The lab develops innovative strategies for site-selective functionalization of C–H bonds in indoles, indolines, and anilines using diverse coupling partners such as diazo compounds, amination agents, and olefins. Their work emphasizes atom-economical, step-efficient synthesis of medicinally relevant scaffolds, including cyanated, aminated, and alkenylated heterocycles with high functional group tolerance. The research also extends to the synthesis of biologically active compounds, including anticancer agents, through strategic C–H activation and cyclization processes.
Figures are computed from collected data and may differ slightly.
The linear or branched allyl moieties on aromatic rings are well-known as ubiquitous structural motifs found in a range of natural products and medicinally relevant molecules. They also represent an important class of organic intermediates for the transformation of an olefin group into many useful functional groups. Established methods for the installation of allylic groups rely primarily on nucleophilic substitution or transmetalation of aryl metal complexes to allyl electrophiles, Lewis acid-m
The rhodium(III)-catalyzed direct functionalization of aniline C-H bonds with α-diazo compounds is described. These transformations provide a facile construction of ortho-alkylated anilines with diazo malonates or highly substituted indoles with diazo acetoacetates.
Abstract The rhodium‐catalyzed selective cyanation of CH bonds of indolines and indoles with N ‐cyano‐ N ‐phenyl‐ para ‐methylbenzenesulfonamide is described. This protocol offers a facile access to C‐7 cyanated indolines and C‐2 cyanated indoles with high site selectivity and excellent functional group tolerance. magnified image
Abstract The site‐selective C−H amination reaction of 7‐azaindoles with various benzisoxazoles as amination surrogates under cationic rhodium(III) catalysis is described. This transformation efficiently provides a range of ortho ‐aminated N ‐aryl‐7‐azaindoles with excellent site‐selectivity and functional group compatibility. The formed ortho ‐aminated 7‐azaindoles were readily transformed into biologically relevant heterocycles such as azaindoloacridine, azaindoloacridone, and bis‐indole compou
The pyrimidinyl-directed C–H functionalization of indolines with anthranils as amination sources under rhodium(<sc>iii</sc>) catalysis is described to afford a range of C7-aminated indoline derivatives with excellent site-selectivity and functional group compatibility.
The rhodium-catalyzed oxidative alkenylation of N-benzyltriflamides with olefins followed by an intramolecular cyclization via C-H bond activation is described. This method results in the direct and efficient synthesis of highly substituted isoindoline frameworks.
The Rh(III)-catalyzed C-H functionalization and subsequent intramolecular cyclization between azobenzenes and vinylene carbonate is described herein. Depending on the electronic property of azobenzenes, this transformation results in the formation of (2<i>H</i>)-indazoles or dihydrocinnolin-4-ones through the generation of <i>ortho</i>-alkylated azo-intermediates followed by decarboxylation. Surprisingly, vinylene carbonate acts as an acetaldehyde or acetyl surrogate to enable the [4 + 1] or [4
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