Ligand‐Assisted Pd‐Catalyzed N‐Dealkylative Carbonylation of Tertiary Amines with (Hetero)Aryl Halides to Tertiary Amides

This work reports an efficient synthesis of tertiary amides using a ligand‐assisted Pd‐catalyzed carbonylation of (hetero)aryl halides with tertiary amines. A key step in this reaction is C(sp3)−N bond cleavage using CuO as an oxidant. The reaction proceeds with high efficiency employing a bidentate...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2018-01, Vol.7 (1), p.160-164
Main Authors: Mane, Rajendra S., Bhanage, Bhalchandra M.
Format: Article
Language:English
Subjects:
Amides
Amines
Aromatic compounds
aryl bromides
Carbon monoxide
carbonylation
Carbonyls
Chemical industry
Chemical synthesis
C−N bond cleavage
Halides
Ligands
Organic chemistry
Palladium
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Summary:This work reports an efficient synthesis of tertiary amides using a ligand‐assisted Pd‐catalyzed carbonylation of (hetero)aryl halides with tertiary amines. A key step in this reaction is C(sp3)−N bond cleavage using CuO as an oxidant. The reaction proceeds with high efficiency employing a bidentate phosphine ligand (dppp), which is a key for the carbonylation of unreactive (hetero)aryl halides and series of tertiary amines at atmospheric pressure of carbon monoxide. In combination with: A general and efficient synthesis of tertiary amides using a bidentate phosphine ligand‐assisted Pd‐catalyzed carbonylation of (hetero)aryl halides with tertiary amines has been demonstrated. A key step in this reaction is C(sp3)−N bond cleavage of tertiary amines using CuO as an oxidant.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201700574