Yonsei University · Chemistry
Professor Ikyon Kim's research lab specializes in the development of innovative, atom-economical, and catalytic methodologies for the synthesis of complex heterocyclic frameworks prevalent in natural products and bioactive molecules. The lab focuses on transition-metal-catalyzed and metal-free domino reactions, including C–H activation, cyclizations, and multicomponent couplings, to efficiently construct benzofurans, indolizines, and related polycyclic systems. A central theme is the strategic functionalization of heterocycles to access medicinally relevant scaffolds with high regio- and stereoselectivity under mild, eco-friendly conditions. The work consistently emphasizes synthetic efficiency, step economy, and the creation of novel molecular architectures difficult to access by traditional methods.
Figures are computed from collected data and may differ slightly.
A highly practical route to oligostilbenoid natural products is described. A regioselective Bi(OTf)3-catalyzed cyclodehydration provided ready access to 3-arylbenzofuran. Pd-catalyzed direct C-H activation of benzofuran and subsequent cross-coupling with aryl halide was successfully implemented for the introduction of aryl group at the C2 position of benzofuran. Further manipulation of the 2,3-diarylbenzofuran led to the efficient total synthesis of permethylated analogues of viniferifuran, mali
A highly efficient and atom-economical construction of 2-substituted 5-hydroxybenzofurans was accomplished by employing a platinum-catalyzed domino dienone-phenol rearrangement/5-endo-dig cyclization reaction of quinols bearing alkynes.
A direct one-pot approach to polysubstituted indolizinones from tertiary propargylic alcohols using a palladium-catalyzed domino process involving aminopalladation, reductive elimination, and 1,2-shift is described.
The strategic use of a sequential Sonogashira coupling/intramolecular alkyne-carbonyl metathesis process for the synthesis of a pyridine ring from 1-(2-haloaryl)-1H-pyrrole-2-carbaldehydes allowed ready access to diverse novel benzo-fused indolizines, pyrrolo[1,2-a]quinolines, in good to excellent yields. As a hybrid structure of indolizine and quinoline, the resulting scaffold has an acyl substituent at the C5 position, which is difficult to make by any other known approaches.
Post-functionalization at the C3 position of indolizines via In(iii)-catalyzed three-component coupling reaction with amines and aldehydes allowed rapid access to a new class of indolizines with diverse functional groups at the C3 position in good to excellent yields.
A domino Michael-aldol double elimination route to indolizines having two different acyl groups at the C5 and C7 positions is described where chromone is employed as a two-carbon unit for the synthesis of a pyridine moiety for the first time. Various analogues were readily accessed in good yields under metal-free and eco-friendly conditions. Further manipulation of the resulting products allowed entry to novel indolizine-heterocycle adducts, which are difficult to access by other methods.
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