Issue 11, 2012

Pd(ii)-catalyzed cycloisomerisation of γ-alkynoic acids and one-pot tandem cycloisomerisation/CuAAC reactions in water

Abstract

Cycloisomerisation reactions of γ-alkynoic acids into cyclic enol-lactones can be conveniently performed in pure water as a solvent and under aerobic conditions by using a novel iminophosphorane–Pd(II) complex trans-[PdCl22-N,S-(PTA)[double bond, length as m-dash]NP([double bond, length as m-dash]S)(OEt)2}]2 as a catalyst. It is important to note that the catalytic system could be recycled up to 10 consecutive runs. In addition and for the first time, a one-pot tandem orthogonal reaction involving the fast cycloisomerisation of γ-alkynoic acids, followed by an intermolecular atom economical process, i.e. the 1,3-dipolar cycloaddition of azides with terminal alkynes (CuAAC), is reported. This new tandem cycloisomerisation/click reaction proceeds also in water, at room temperature and under aerobic conditions, giving rise to unprecedented bicyclic triazol-enol-lactones under the principles of the so called “Green Chemistry”.

Graphical abstract: Pd(ii)-catalyzed cycloisomerisation of γ-alkynoic acids and one-pot tandem cycloisomerisation/CuAAC reactions in water

Supplementary files

Article information

Article type
Paper
Submitted
27 Jul 2012
Accepted
06 Sep 2012
First published
07 Sep 2012

Green Chem., 2012,14, 3190-3196

Pd(II)-catalyzed cycloisomerisation of γ-alkynoic acids and one-pot tandem cycloisomerisation/CuAAC reactions in water

J. García-Álvarez, J. Díez and C. Vidal, Green Chem., 2012, 14, 3190 DOI: 10.1039/C2GC36176K

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