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Title: NH2 as a directing group: from the unexpected cyclopalladation of aminoesters to the preparation of benzolactams by Pd(II)-catalyzed carbonylation of N-unprotected arylethylamines
Author: Albert Mach, Joan
Ariza Piquer, Xavier
Calvet Pallàs, Maria Teresa
Font Bardia, Ma. Mercedes
García Gómez, Jordi
Granell Sanvicente, Jaime Ramón
Lamela, Andrea
López, Blanca
Martínez López, Manuel, 1957-
Ortega, Laura
Rodríguez Ramírez, Aleix
Santos, David
Keywords: Pal·ladi (Element químic)
Cinètica química
Compostos organometàl·lics
Chemical kinetics
Organometallic compounds
Issue Date: 2013
Publisher: American Chemical Society
Abstract: An unusual NH2-directed Pd(II)-catalytic carbonylation of quaternary aromatic α-amino esters to yield benzolactams has been developed. The steric hindrance around the amino group is pivotal for the success of the process. The stoichiometric cyclometallation of a variety amino esters has been studied in order to evaluate the influence of the different variables (size of the metallacycle, aromatic ring substituents, and steric bulk) in the process, and a complete kinetico-mechanistic study of the cyclopalladation process has been carried out. The experimental results indicate that the full substitution of the carbon in the α position of the amino esters plays an important role in their cyclopalladation reaction. The reaction shows a strong bias to 6-membered lactams over the 5-membered analogues, which can be explained by a greater reactivity of the six-membered palladacycles.
Note: Versió postprint del document publicat a:
It is part of: Organometallics, 2013, vol. 32, num. 2, p. 649-659
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ISSN: 0276-7333
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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