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Nonclassical Mechanism in the Cyclodehydration of Diols Catalyzed by a Bifunctional Iridium Complex
Author(s) -
González Miera Greco,
Bermejo López Aitor,
MartínezCastro Elisa,
Norrby PerOla,
MartínMatute Belén
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201805460
Subject(s) - bifunctional , iridium , cationic polymerization , chemistry , nucleophile , carbene , hydride , catalysis , enantioselective synthesis , mechanism (biology) , combinatorial chemistry , medicinal chemistry , metal , stereochemistry , polymer chemistry , organic chemistry , philosophy , epistemology
1,4‐ and 1,5‐diols undergo cyclodehydration upon treatment with cationic N‐heterocyclic carbene (NHC)–Ir III complexes to give tetrahydrofurans and tetrahydropyrans, respectively. The mechanism was investigated, and a metal‐hydride‐driven pathway was proposed for all substrates, except for very electron‐rich ones. This contrasts with the well‐established classical pathways that involve nucleophilic substitution.