Palladium-Catalyzed Dehydrative Cross-Coupling of Allylic Alcohols and N-Heterocycles Promoted by a Bicyclic Bridgehead Phosphoramidite Ligand and an Acid Additive

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A mild and efficient dehydrative cross-coupling reaction between allylic alcohols and N-heterocycles using palladium catalysis is reported. A bicyclic bridgehead phosphoramidite (briphos) ligand together with Pd(dba)(2) is a highly efficient catalyst, and an acid additive involved in the rate-determining step promotes the catalytic cycle. The coupling reaction of allylic alcohols with N-heterocycles including imidazoles, benzimidazoles, and triazole proceeds under mild reaction conditions with high yields using Pd/briphos and pentafluorophenol.
Publisher
AMER CHEMICAL SOC
Issue Date
2016-02
Language
English
Article Type
Article
Keywords

AQUEOUS-MEDIA; BOND-CLEAVAGE; AMINO-ACID; ALLYLATION; AMINATION; SUBSTITUTION; ACTIVATION; WATER; NUCLEOPHILES; COMPLEXES

Citation

ORGANIC LETTERS, v.18, no.3, pp.616 - 619

ISSN
1523-7060
DOI
10.1021/acs.orglett.6b00001
URI
http://hdl.handle.net/10203/207426
Appears in Collection
CH-Journal Papers(저널논문)
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