Palladium/phenanthroline catalyzed reduction of nitroarenes by in situ-generated carbon monoxide, from the decomposition of phenyl formate, affords the corresponding nitrosoarenes. The latter are trapped by conjugated dienes to give the corresponding 3,6-dihydro-2H-[1, 2]-oxazines (hetero Diels-Alder adducts). Many functional groups are well tolerated. Yields are higher than those obtainable by any previously reported method, including the direct reaction of the diene with the pure nitrosoarene. The reaction can be performed in a single standard glass pressure tube, without the need for autoclaves or high-pressure CO lines.
Synthesis of 3,6-Dihydro-2H-[1, 2]-Oxazines from Nitroarenes and Conjugated Dienes, Catalyzed by Palladium/Phenanthroline Complexes and Employing Phenyl Formate as a CO Surrogate / M.A. EL-Atawy, D. Formenti, F. Ferretti, F. Ragaini. - In: CHEMCATCHEM. - ISSN 1867-3880. - 10:20(2018 Oct 23), pp. 4707-4717.
|Titolo:||Synthesis of 3,6-Dihydro-2H-[1, 2]-Oxazines from Nitroarenes and Conjugated Dienes, Catalyzed by Palladium/Phenanthroline Complexes and Employing Phenyl Formate as a CO Surrogate|
RAGAINI, FABIO ATTILIO CIRILLO (Corresponding)
|Parole Chiave:||CO surrogate; Hetero-Diels-Alder reaction; N-ligands; Nitroarenes; Palladium; Catalysis; Physical and Theoretical Chemistry; Organic Chemistry; Inorganic Chemistry|
|Settore Scientifico Disciplinare:||Settore CHIM/03 - Chimica Generale e Inorganica|
Settore CHIM/06 - Chimica Organica
|Data di pubblicazione:||23-ott-2018|
|Data ahead of print / Data di stampa:||22-ago-2018|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1002/cctc.201801223|
|Appare nelle tipologie:||01 - Articolo su periodico|