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Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy
Authors:Hideyasu China  Ravi Kumar  Kotaro Kikushima  Toshifumi Dohi
Institution:1.Department of Medical Bioscience, Nagahama Institute of Bio-Science and Technology, 1266, Tamuracho Nagahama-shi, Shiga 526-0829, Japan;2.Department of Chemistry, J. C. Bose University of Science & Technology, YMCA, NH-2, Sector-6, Mathura Road, Faridabad, Haryana 121006, India;3.College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-0058, Japan;
Abstract:In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties by generating halonium intermediates, followed by the attack of carbon-containing, nitrogen-containing, oxygen-containing, and sulfur-containing nucleophiles to give highly functionalized carbocycles and heterocycles. New transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products, according to the difference in the size and number of halogen atoms, have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis.
Keywords:intramolecular cyclization  halocyclization  halogen intermediate  reagent switch  organocatalyst  substrate switch  endo/exo selectivity
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