http://www.cnr.it/ontology/cnr/individuo/prodotto/ID174895

A Palladium Iodide-Catalyzed Carbonylative Approach to Functionalized Pyrrole Derivatives (Articolo in rivista)

Type

Prodotto della ricerca (Classe)
Articolo in rivista (Classe)

Label

A Palladium Iodide-Catalyzed Carbonylative Approach to Functionalized Pyrrole Derivatives (Articolo in rivista) (literal)

Anno

2012-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

10.1021/jo300365n (literal)

Alternative label

Bartolo Gabriele (1); Lucia Veltri (2); Raffaele Mancuso (2); Giuseppe Salerno (2); Sabino Maggi (3); Brunella Aresta (3) (2012)
A Palladium Iodide-Catalyzed Carbonylative Approach to Functionalized Pyrrole Derivatives
in Journal of organic chemistry; ACS, American chemical society, Washington, DC (Stati Uniti d'America)
(literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

Bartolo Gabriele (1); Lucia Veltri (2); Raffaele Mancuso (2); Giuseppe Salerno (2); Sabino Maggi (3); Brunella Aresta (3) (literal)

Pagina inizio

4005 (literal)

Pagina fine

4016 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url

http://pubs.acs.org/doi/abs/10.1021/jo300365n (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

77 (literal)

Rivista

Journal of organic chemistry (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali

12 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo

8 (literal)

Note

ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

(1) Dipartimento di Scienze Farmaceutiche, Universita' della Calabria, I-87036 Arcavacata di Rende (CS), Italy; (2) Dipartimento di Chimica, Universita' della Calabria, I-87036 Arcavacata di Rende (CS), Italy; (3) CNR Istituto di Cristallografia, Via Amendola, 122/O, I-70124 Bari, Italy; (literal)

Titolo

A Palladium Iodide-Catalyzed Carbonylative Approach to Functionalized Pyrrole Derivatives (literal)

Abstract

A novel and convenient approach to functionalized pyrroles is presented, based on Pd-catalyzed oxidative heterocyclization-alkoxycarbonylation of readily available N-Boc-1-amino-3-yn-2-ols. Reactions were carried out in alcoholic solvents at 80-100 °C and under 20 atm (at 25 °C) of a 4:1 mixture of CO-air, in the presence of the PdI2-KI catalytic system (2-5 mol % of PdI2, KI/PdI2 molar ratio = 10). In the case of N-Boc-1-amino-3-yn-2-ols 3, bearing alkyl or aryl substituents, the carbonylation reaction led to a mixture of Boc-protected and N-unsubstituted pyrrole-3-carboxylic esters 4 and 5, respectively. This mixture could be conveniently and quantitatively converted into deprotected pyrrole-3-carboxylic esters 5 by a simple basic treatment. In the case of diastereomeric (3RS,4RS)- and (3RS,4SR)-N-Boc-3-amino-2-methyldec-5-yn-4-ol (syn-3f and anti-3f, respectively, whose relative configuration was determined by X-ray crystallographic analysis), no particular difference was observed in the reactivity of the two diastereomers between them and with respect to the diastereomeric mixture (3S,4S) + (3S,4R). Interestingly, N-Boc-2-alkynyl-1-amino-3-yn-2-ols 6, bearing an additional alkynyl substituent ? to the hydroxyl group, spontaneously underwent N-deprotection under the reaction conditions and regioselective water addition to the alkynyl group at C-3 of the corresponding pyrrole-3-carboxylic ester derivative, thus directly affording highly functionalized pyrrole derivatives 7 in one step. (literal)

Editore