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

被引：43

作者：

Maibunkaew, Tapanee ^{[1
]}

Thongsornkleeb, Charnsak ^{[1
,2
]}

Tummatorn, Jumreang ^{[2
]}

Bunrit, Anon ^{[2
]}

Ruchirawat, Somsak ^{[1
,2
]}

机构：

[1] Minist Educ, Program Chem Biol, Chulabhorn Grad Inst, Ctr Excellence Environm Hlth & Toxicol,CHE, 54 Kampang Phet 6, Bangkok 10210, Thailand

[2] Chulabhorn Res Inst, Bangkok 10210, Thailand

来源：

SYNLETT | 2014年 / 25卷 / 12期

关键词：

interhalogens; electrophilic aromatic halogenation; isocryptolepine; chlorotrimethylsilane; N-halosuccinimide; ALKALOIDS; IODOSUCCINIMIDE; ISOCRYPTOLEPINE; CHLORINATION; MILD;

D O I：

10.1055/s-0034-1378225

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1769 / 1775

页数：7

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