23364-15-0Relevant academic research and scientific papers
NH2 as a directing group: From the cyclopalladation of amino esters to the preparation of benzolactams by palladium(II)-catalyzed carbonylation of N-unprotected arylethylamines
Albert, Joan,Ariza, Xavier,Calvet, Teresa,Font-Bardia, Merce,Garcia, Jordi,Granell, Jaume,Lamela, Andrea,Lopez, Blanca,Martinez, Manuel,Ortega, Laura,Rodriguez, Aleix,Santos, David
, p. 649 - 659 (2013/03/14)
An unusual NH2-directed Pd(II)-catalyzed 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 cyclometalation 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 toward six-membered lactams over the five-membered analogues, which can be explained by a greater reactivity of the six-membered palladacycles.
Pd(ii)-catalyzed carbonylation of N-unprotected arylethylamines
Lopez, Blanca,Rodriguez, Aleix,Santos, David,Albert, Joan,Ariza, Xavier,Garcia, Jordi,Granell, Jaume
supporting information; experimental part, p. 1054 - 1056 (2011/02/25)
An unprecedented NH2-directed Pd(ii)-catalytic carbonylation of quaternary aromatic α-amino esters to yield 6-membered benzolactams has been developed. The reaction shows a strong bias to 6-membered lactams over 5-membered ones. The steric hind
