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
收藏
页码：7510 / 7513
页数：4
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