Synthesis and characterization of novel pyridine–isourea complexes of Pd(II)

Bortoluzzi, Marco; Paolucci, Gino; Sartor, Federica; Bertolasi, Valerio

doi:10.1016/j.poly.2012.02.014

Cited by 4 publications

(1 citation statement)

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“…DCC/CuCl reacts with 2-hydroxyimines and nitroaldols to afford 2,3-enimines and nitroalkenes [7,8]. Isoureas, useful alkylating agents also involved in the preparation of heterocyclic compounds, are commonly obtained from the reaction of carbodiimides with alcohols in the presence of catalytic CuX [9][10][11][12][13][14][15]. The mild reaction conditions typical of Cu(I) catalysis provide an alternative and selective synthetic approach with respect to the utilization of Brønsted acids, that can promote oligomerization or interfere with other functional groups.…”

Section: Introductionmentioning

confidence: 99%

Influence of Copper(I) Halides on the Reactivity of Aliphatic Carbodiimides

Bortoluzzi

2020

The 24th International Electronic Conference on Synthetic Organic Chemistry

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The influence of copper(I) halides CuX (X = Cl, Br, I) on the electronic structure of N,N′-diisopropylcarbodiimide (DICDI) and N,N′-dicyclohexylcarbodiimide (DCC) was investigated by means of computational DFT (density functional theory) methods. The coordination of the considered carbodiimides occurs by one of the nitrogen atoms, with the formation of linear complexes having a general formula of [CuX(carbodiimide)]. Besides varying the carbon–nitrogen bond lengths, the thermodynamically favourable interaction with Cu(I) reduces the electron density on the carbodiimides and alters the energies of the (NCN)-centred, unoccupied orbitals. A small dependence of these effects on the choice of the halide was observable. The computed Fukui functions suggested negligible interaction of Cu(I) with incoming nucleophiles, and the reactivity of carbodiimides was altered by coordination mainly because of the increased electrophilicity of the {NCN} fragments.

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