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Synfacts 2016; 12(2): 0205
DOI: 10.1055/s-0035-1561138
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Direct Cross-Coupling of Phenols with Amines Using Palladium on Carbon

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Rikako Ishii
Chen Z, Zeng H, Girard SA, Wang F, Chen N, Li C.-J * McGill University, Montreal, Canada
Formal Direct Cross-Coupling of Phenols with Amines.

Angew. Chem. Int. Ed. 2015;
54: 14487-14491
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Further Information

Publication History

Publication Date:
19 January 2016 (online)

 
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Key words

palladium on carbon - cross-coupling - phenols - amines

Significance

Palladium on carbon catalyzed the formal dehydrative direct cross-coupling of phenols with amines in the presence of sodium formate and trifluoroacetic acid in toluene to give the corresponding secondary or tertiary amines in ≤90% yield (33 examples).


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Comment

When biphenol was used as the substrate, only one C–N bond was formed (3p), whereas two C–N bonds were formed in the reaction of resorcinol (3q). Product 3u, bearing an ester group, was obtained without ester–amine exchange. A nitrogen-containing heterocyclic product 3w was obtained from the reaction of catechol with cyclohexane-1,2-diamine.


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