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Iron‐Catalyzed Ring‐Closing C−O/C−O Metathesis of Aliphatic Ethers
Author(s) -
Biberger Tobias,
Makai Szabolcs,
Lian Zhong,
Morandi Bill
Publication year - 2018
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.201802563
Subject(s) - metathesis , ring closing metathesis , oxonium ion , chemistry , salt metathesis reaction , catalysis , context (archaeology) , combinatorial chemistry , organic chemistry , polymerization , biology , ion , paleontology , polymer
Among all metathesis reactions known to date in organic chemistry, the metathesis of multiple bonds such as alkenes and alkynes has evolved into one of the most powerful methods to construct molecular complexity. In contrast, metathesis reactions involving single bonds are scarce and far less developed, particularly in the context of synthetically valuable ring‐closing reactions. Herein, we report an iron‐catalyzed ring‐closing metathesis of aliphatic ethers for the synthesis of substituted tetrahydropyrans and tetrahydrofurans, as well as morpholines and polycyclic ethers. This transformation is enabled by a simple iron catalyst and likely proceeds via cyclic oxonium intermediates.