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Synlett 2014; 25(12): 1769-1775
DOI: 10.1055/s-0034-1378225
letter
© Georg Thieme Verlag Stuttgart · New York

Practical and Metal-Free Electrophilic Aromatic Halogenation by Inter­halogen Compounds Generated In Situ from N-Halosuccinimide and Catalytic TMSCl

Tapanee Maibunkaew
a   Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology, CHE, Ministry of Education, 54 Kampang Phet 6, Laksi, Bangkok 10210, Thailand
,
Charnsak Thongsornkleeb*
a   Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology, CHE, Ministry of Education, 54 Kampang Phet 6, Laksi, Bangkok 10210, Thailand
b   Chulabhorn Research Institute, 54 Kampang Phet 6, Laksi, Bangkok 10210, Thailand   Fax: +66(2)5538545   Email: charnsak@cri.or.th
,
Jumreang Tummatorn
b   Chulabhorn Research Institute, 54 Kampang Phet 6, Laksi, Bangkok 10210, Thailand   Fax: +66(2)5538545   Email: charnsak@cri.or.th
,
Anon Bunrit
b   Chulabhorn Research Institute, 54 Kampang Phet 6, Laksi, Bangkok 10210, Thailand   Fax: +66(2)5538545   Email: charnsak@cri.or.th
,
Somsak Ruchirawat
a   Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology, CHE, Ministry of Education, 54 Kampang Phet 6, Laksi, Bangkok 10210, Thailand
b   Chulabhorn Research Institute, 54 Kampang Phet 6, Laksi, Bangkok 10210, Thailand   Fax: +66(2)5538545   Email: charnsak@cri.or.th
› Author Affiliations
Further Information

Publication History

Received: 28 March 2014

Accepted after revision: 01 May 2014

Publication Date:
05 June 2014 (online)

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Abstract

Halomonochloride compounds (ClCl, BrCl, ICl) generated in situ from N-halosuccinimide and catalytic chlorotrimethylsilane (TMSCl, 0.1 equiv) can efficiently halogenate aromatic compounds to give halogenated products in good to excellent yields and selectivities. The reaction can be carried out at room temperature or at lower temperatures, requires only one hour, is practical to apply to a wide range of substrates, and provides a simple access to a variety of haloarene compounds.

Key words

interhalogens - electrophilic aromatic halogenation - isocryptolepine - chlorotrimethylsilane - N-halosuccinimide

Supporting Information

    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
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  • References and Notes

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