Practical, Modular, and General Synthesis of Benzofurans through Extended Pummerer Annulation/Cross-Coupling Strategy

被引：104

作者：

Murakami, Kei ^{[1
,2
]}

Yorimitsu, Hideki ^{[1
,3
]}

Osuka, Atsuhiro ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

[2] Kyoto Univ, Hakubi Ctr Adv Res, Kyoto 6068502, Japan

[3] ACT C Japan Sci & Technol Agcy, Kyoto, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 29期

关键词：

annulation; heterocycles; nickel; rearrangement; synthetic methods; ARYLKETENE DITHIOACETAL MONOXIDES; CLAISEN REARRANGEMENT SEQUENCE; NUCLEOPHILIC ORTHO-ALLYLATION; UNACTIVATED INTERNAL ALKYNES; OXIDATIVE ANNULATION; EFFICIENT SYNTHESIS; CARBONYL-COMPOUNDS; GRIGNARD-REAGENTS; BOND FORMATION; PHENOLS;

D O I：

10.1002/anie.201403288

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Operationally simple, efficient, and widely applicable Pummerer annulations of simple phenols with ketene dithioacetal monoxides, with the aid of trifluoroacetic anhydride, have been shown to provide a variety of benzofurans having a methylthio group at the 2-position. Subsequent and newly developed nickel-catalyzed arylation at the methylthio group culminates in diversity-oriented synthesis of multisubstituted benzofurans. Our extended Pummerer annulation/cross-coupling sequence is powerful enough to synthesize biologically active natural products as well as highly fluorescent benzofuran derivatives.

引用

页码：7510 / 7513

页数：4

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