Synthesis of tetrasubstituted 2-aryl-3-arylsulfonyl pyrroles:: Unexpected regioselectivity in directed ortho-metallation reactions

被引：6

作者：

Bailey, Nick ^{[1
]}

Demont, Emmanuel ^{[1
]}

Garton, Neil ^{[1
]}

Seow, Hui-Xian ^{[1
]}

机构：

[1] GlaxoSmithKline Inc, Neurol & Gastrointestinal Ctr Excellence Drug Dis, New Frontiers Sci Pk, Harlow CM19 5AW, Essex, England

来源：

SYNLETT | 2008年 / 02期

关键词：

phenylsulfonyl fluoride; 3-sulfonyl pyrrole; directed; ortho-metallation; palladium; Suzuki coupling;

D O I：

10.1055/s-2007-1000880

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Arylsulfonyl pyrroles can be readily obtained from 3-Br-TIPS pyrrole via halogen-metal exchange and subsequent sulfonylation. The regioselectivity of the subsequent directed ortho-metallation (DOM) reaction in order to functionalise the C-2 position depends on the nature of the base (LTMP, n- or s-BuLi) and the N-substituent (SEM or Boc) used. The bulk of the N-substituent also strongly influences the yield of the subsequent Suzuki coupling with 2-iodo-3-arylsulfonyl pyrrole derivatives.

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收藏

页码：185 / 188

页数：4

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