Decarboxylative Benzylation of Aryl and Alkenyl Boronic Esters

The copper‐catalyzed decarboxylative benzylation of aryl and alkenyl boronic esters with electron‐deficient aryl acetates is reported. The oxidative coupling proceeds under mild, aerobic conditions and tolerates a host of potentially reactive electrophilic functional groups that would be problematic...

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Bibliographic Details
Published in:Angewandte Chemie 2018-04, Vol.130 (17), p.4702-4706
Main Authors: Moon, Patrick J., Fahandej‐Sadi, Anis, Qian, Wenyu, Lundgren, Rylan J.
Format: Article
Language:English
Subjects:
Acetates
Acetic acid
Aerobe Katalyse
Aerobic conditions
Aldehydes
Aromatic compounds
Bor
Bromides
Chemistry
Decarboxylation
Decarboxylierungen
Esters
Functional groups
Iodides
Kreuzkupplungen
Kupfer
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Summary:The copper‐catalyzed decarboxylative benzylation of aryl and alkenyl boronic esters with electron‐deficient aryl acetates is reported. The oxidative coupling proceeds under mild, aerobic conditions and tolerates a host of potentially reactive electrophilic functional groups that would be problematic with traditional benzylation methods (aryl iodides and bromides, protic heteroatoms, aldehydes, Michael acceptors). A reaction pathway in which a benzylic nucleophile is generated by aryl acetate decarboxylation and in turn is intercepted by the catalyst to form diarylmethane products is supported by mechanistic studies. An der Luft: Die Kupfer‐katalysierte decarboxylierende Benzylierung von Aryl‐ und Alkenylboronsäureestern mit elektronenarmen Arylacetaten gelingt unter milden aeroben Bedingungen. Viele reaktive, elektrophile funktionelle Gruppen werden toleriert, deren Einsatz in gewöhnlichen Benzylierungen problematisch ist.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201800829