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Practical, Modular, and General Synthesis of Benzofurans through Extended Pummerer Annulation/Cross‐Coupling Strategy
Author(s) -
Murakami Kei,
Yorimitsu Hideki,
Osuka Atsuhiro
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201403288
Subject(s) - benzofuran , ketene , annulation , trifluoroacetic anhydride , chemistry , pummerer rearrangement , combinatorial chemistry , organic chemistry , acetic anhydride , catalysis
Abstract 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.