Journal
TETRAHEDRON LETTERS
Volume 63, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2020.152689
Keywords
N-Chloro-N-(phenylsulfonyl)benzene sulfonamide; Eco-friendly chlorination; Arenes; Activator free; N-Chloro reagents
Categories
Funding
- Department of Science and Technology, India (WOS-A)
- Loba Chemie Pvt. Ltd.
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NCBSI has been explored as a chlorinating reagent for direct chlorination of activated arenes and heterocycles without activator, showing high reactivity and potential for recycling precursor from aqueous spent, also applicable for eco-friendly synthesis of chloroxylenol.
N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent. (C) 2020 Elsevier Ltd. All rights reserved.
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