Allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions

Allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions

The allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions is described. The synergistic palladium/copper-catalyzed reaction of aromatic aldehydes, allylic carbonates, and a silylboronate produces the corresponding homoallylic alcohol derivatives. This process involves the catalytic...

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Veröffentlicht in:Beilstein journal of organic chemistry 2020-02, Vol.16 (1), p.185-189
Hauptverfasser: Yuasa, Akihiro, Nagao, Kazunori, Ohmiya, Hirohisa
Format: Artikel
Sprache:eng
Schlagworte:
aldehyde
Chemistry
copper
copper catalysis
cross-coupling
Letter
palladium
synthetic method
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Zusammenfassung:The allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions is described. The synergistic palladium/copper-catalyzed reaction of aromatic aldehydes, allylic carbonates, and a silylboronate produces the corresponding homoallylic alcohol derivatives. This process involves the catalytic formation of a nucleophilic α-silyloxybenzylcopper(I) species and the subsequent palladium-catalyzed allylic substitution.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.16.21