An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters

An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters

The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-α-iminoesters affords aryl carboxylic esters via carbonyl-imino σ bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism s...

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Veröffentlicht in:Organic & biomolecular chemistry 2013-09, Vol.11 (36), p.6013-6022
Hauptverfasser: Qian, Cheng, Chen, Jiayan, Fu, Meiqin, Zhu, Shiya, Chen, Wen-Hua, Jiang, Huanfeng, Zeng, Wei
Format: Artikel
Sprache:eng
Schlagworte:
Boronic Acids - chemistry
Catalysis
Esters - chemical synthesis
Esters - chemistry
Imines - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Palladium - chemistry
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Zusammenfassung:The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-α-iminoesters affords aryl carboxylic esters via carbonyl-imino σ bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism studies have revealed that an unusual 1,2-aryl shift process is involved in the transformation.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob41011k