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

Tapanee Maibunkaew; Charnsak Thongsornkleeb; Jumreang Tummatorn; Anon Bunrit; Somsak Ruchirawat

doi:10.1055/s-0034-1378225

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(12): 1769-1775
DOI: 10.1055/s-0034-1378225

letter

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

Authors

Tapanee Maibunkaew

^aProgram 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*

^aProgram 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

^bChulabhorn Research Institute, 54 Kampang Phet 6, Laksi, Bangkok 10210, Thailand Fax: +66(2)5538545 eMail: charnsak@cri.or.th
Jumreang Tummatorn

^bChulabhorn Research Institute, 54 Kampang Phet 6, Laksi, Bangkok 10210, Thailand Fax: +66(2)5538545 eMail: charnsak@cri.or.th
Anon Bunrit

^bChulabhorn Research Institute, 54 Kampang Phet 6, Laksi, Bangkok 10210, Thailand Fax: +66(2)5538545 eMail: charnsak@cri.or.th
Somsak Ruchirawat

^aProgram 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

^bChulabhorn Research Institute, 54 Kampang Phet 6, Laksi, Bangkok 10210, Thailand Fax: +66(2)5538545 eMail: charnsak@cri.or.th

Abstract

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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

Volltext

Referenzen

References and Notes

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20 Garcia P, Lau YY, Perry MR, Schafer LL. Angew. Chem. Int. Ed. 2013; 52: 9144

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

Authors

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