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Sodium halides as the source of electrophilic halogens in green synthesis of 3-halo- and 3,n-dihalobenzo[b]thiophenes.


ABSTRACT: A convenient methodology for the synthesis of mono- and di-halogenated benzo[b]thiophenes is described herein, which utilizes copper(II) sulfate pentahydrate and various sodium halides in the presence of substituted 2-alkynylthioanisoles. The proposed method is facile, uses ethanol as a green solvent, and results in uniquely substituted benzo[b]thiophene structures with isolated yields up to 96%. The most useful component of this methodology is the selective introduction of bromine atoms at every available position (2-7) around the benzo[b]thiophene ring, while keeping position 3 occupied by a specific halogen atom such as Cl, Br or I. Aromatic halogens are useful reactive handles; therefore, the selective introduction of halogens at specific positions would be valuable in the targeted synthesis of bioactive molecules and complex organic materials via metal-catalyzed cross coupling reactions. This work is a novel approach towards the synthesis of dihalo substituted benzo[b]thiophene core structures, which provides a superior alternative to the current methods discussed herein.

SUBMITTER: Kesharwani T 

PROVIDER: S-EPMC6420224 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Sodium halides as the source of electrophilic halogens in green synthesis of 3-halo- and 3,<i>n</i>-dihalobenzo[<i>b</i>]thiophenes.

Kesharwani Tanay T   Kornman Cory C   Tonnaer Amanda A   Hayes Amanda A   Kim Seoyoung S   Dahal Nikesh N   Romero Ralf R   Royappa Andrew A  

Tetrahedron 20180426 24


A convenient methodology for the synthesis of mono- and di-halogenated benzo[<i>b</i>]thiophenes is described herein, which utilizes copper(II) sulfate pentahydrate and various sodium halides in the presence of substituted 2-alkynylthioanisoles. The proposed method is facile, uses ethanol as a green solvent, and results in uniquely substituted benzo[<i>b</i>]thiophene structures with isolated yields up to 96%. The most useful component of this methodology is the selective introduction of bromine  ...[more]

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