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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Published inBeilstein journal of organic chemistry Vol. 16; no. 1; pp. 185 - 189
Main Authors Yuasa, Akihiro, Nagao, Kazunori, Ohmiya, Hirohisa
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 07.02.2020
Subjects
aldehyde
Chemistry
copper
copper catalysis
cross-coupling
Letter
palladium
synthetic method
cross-coupling
copper catalysis
aldehyde
copper
palladium
synthetic method
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.16.21