Preprint Review Version 1 Preserved in Portico This version is not peer-reviewed

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

Version 1 : Received: 11 December 2020 / Approved: 11 December 2020 / Online: 11 December 2020 (16:48:02 CET)

A peer-reviewed article of this Preprint also exists.

China, H.; Kumar, R.; Kikushima, K.; Dohi, T. Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy. Molecules 2020, 25, 6007. China, H.; Kumar, R.; Kikushima, K.; Dohi, T. Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy. Molecules 2020, 25, 6007.

Journal reference: Molecules 2020, 25, 6007
DOI: 10.3390/molecules25246007

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 via the generation of halonium intermediates, followed by the attack of carbon-, nitrogen-, oxygen-, and sulfur-containing nucleophiles to give highly functionalized carbo- and heterocycles. Interestingly, 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.

Subject Areas

intramolecular cyclization; halocyclization; halogen intermediate; reagent switch; organocatalyst; substrate switch; endo/exo selectivity

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