Two-step, practical, and diversity-oriented synthesis of multisubstituted benzofurans from phenols through Pummerer annulation followed by cross-coupling

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[1] [1,Murakami, Kei
[2] 1,Yorimitsu, Hideki
[3] Osuka, Atsuhiro
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Yorimitsu, Hideki | 1600年 / Chemical Society of Japan卷 / 87期
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Practical and diversity-oriented synthesis of multisubstituted benzofurans has been accomplished from simple phenols through a Pummerer annulation/cross-coupling sequence. Operationally simple and rapid reactions of phenols with ketene dithioacetal monoxides (KDMs) with the aid of trifluoroacetic anhydride provide the corresponding 2-methylsulfanylbenzo[b]furans. The scope of the reaction encompasses phenols and KDMs having a broad range of substituents. The remaining methylsulfanyl group in the annulation products is converted to various aryl groups through cross-coupling reactions that we improved specially to this end. This two-step approach to multisubstituted benzofurans is powerful enough to synthesize highly fluorescent benzofuran derivatives as well as the naturally occurring Eupomatenoid family;
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