Issue 7, 2014

Glycerol: a biorenewable solvent for base-free Cu(i)-catalyzed 1,3-dipolar cycloaddition of azides with terminal and 1-iodoalkynes. Highly efficient transformations and catalyst recycling

Abstract

The combination of CuI and glycerol exhibits a versatile and high catalytic activity in the Huisgen cycloaddition of azides and terminal or 1-iodoalkynes under standard bench experimental conditions (room temperature, under air and in the absence of a base) providing a pivotal contribution to Green Chemistry. Since the catalytic reaction: (i) is amenable at low catalyst loading and accessible on a high scale; (ii) tolerates a variety of functionalities (including the presence of a free thio moiety in the substrate); (iii) can be effectively recycled (up to 6 consecutive runs); and (iv) is isolated in a straightforward manner (by simple filtration in the absence of organic solvents at any stage of the synthesis), the practical application of this methodology provides a complementary synthetic tool to the familiar CuAAC reactions.

Graphical abstract: Glycerol: a biorenewable solvent for base-free Cu(i)-catalyzed 1,3-dipolar cycloaddition of azides with terminal and 1-iodoalkynes. Highly efficient transformations and catalyst recycling

Article information

Article type
Paper
Submitted
13 Mar 2014
Accepted
30 Apr 2014
First published
02 May 2014

Green Chem., 2014,16, 3515-3521

Glycerol: a biorenewable solvent for base-free Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides with terminal and 1-iodoalkynes. Highly efficient transformations and catalyst recycling

C. Vidal and J. García-Álvarez, Green Chem., 2014, 16, 3515 DOI: 10.1039/C4GC00451E

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