Dehydrogenative (Hetero)arene Alkoxylations Triggered by PdII‐Catalyzed C(sp2)–H Activation and Coordinating Substituent: PdII,III or PdIV Complex as Key Intermediate?

This review summarizes the intermolecular PdII‐catalyzed dehydrogenation procedures leading to regioselective coupling of alcohols with (hetero)arenes bearing tethered coordinating groups. Unusual oxidative conditions of catalyst regeneration are required, and the optimum oxidant varies with the sub...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-07, Vol.2017 (25), p.3528-3548
Main Authors: Le Bras, Jean, Muzart, Jacques
Format: Article
Language:English
Subjects:
Alcohols
Alkoxylation
Arenes
Aromatic compounds
Catalysis
Catalysts
Dehydrogenation
Oxidation state
Palladium
Reaction mechanisms
Regeneration
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Summary:This review summarizes the intermolecular PdII‐catalyzed dehydrogenation procedures leading to regioselective coupling of alcohols with (hetero)arenes bearing tethered coordinating groups. Unusual oxidative conditions of catalyst regeneration are required, and the optimum oxidant varies with the substrate. Emphasis is placed on the mechanism of these intriguing reactions. Either PdII–Pd0 or PdII–PdIV redox catalytic cycles, possibly with PdIII intermediates, could be involved, depending on the directing group. ortho‐Alkoxylation of (hetero)arenes bearing tethered coordinating groups is catalyzed by PdII species. According to computational, NMR and ESI‐MS studies, the mechanism should greatly depend on the nature of the coordinating group.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201601592