Pd-catalysed oxidative carbonylation of amino-alcohols to N,N’-bis(hydroxyalkyl) ureas under mild conditions using molecular oxygen as the oxidant

Abstract

A very simple method has been developed for the selective synthesis of symmetrical N,N0- bis(hydroxyalkyl)ureas, OC[NH-(CH2)x-OH]2 (x = 3–6), by oxidative carbonylation of a,v-amino alcohols [3-aminopropanol (3-AP), 4-aminobutanol (4-AB), 5-aminopentanol (5-APe), 6-aminohexanol (6-AH)] with CO/O2 mixtures (O2 = 5 mol%) in the presence of Pd(II)/ligand/NEt3HI catalytic systems. The catalytic process takes place under very mild conditions (p(CO/O2) = 0.1 MPa; 303–333 K). The target products can be isolated in high yield through a very simple and straightforward procedure. The catalytic system can be easily recovered and recycled for several times. The influence of a few reaction parameters (nature of ancillary ligand and iodide co-catalyst, I/Pd molar ratio, etc.) on the catalytic activity has also been investigated and the mainmechanistic features of the catalytic process fully elucidated.


Autore Pugliese

Tutti gli autori

  • QUARANTA E.

Titolo volume/Rivista

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Anno di pubblicazione

2010

ISSN

0926-860X

ISBN

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Numero di citazioni Wos

Nessuna citazione

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Numero di citazioni Scopus

9

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Settori ERC

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Codici ASJC

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