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DOI: 10.1055/s-0032-1317318
Remarkable Activation of an Alkyne [2+2+2]-Cycloaddition Catalyst, 2-Iminomethylpyridine (dipimp)/CoCl2·6H2O/Zn, by a Phthalate Additive
Publication History
Received: 25 July 2012
Accepted after revision: 27 August 2012
Publication Date:
28 September 2012 (online)
![](https://www.thieme-connect.de/media/synlett/201217/lookinside/thumbnails/10.1055-s-0032-1317318-1.jpg)
Abstract
A catalyst for alkyne [2+2+2]-cycloaddition reactions, 2-(2,6-diisopropylphenyl)iminomethylpyridine (dipimp)/CoCl2·6H2O/Zn, can be effectively activated by addition of a catalytic amount of dialkyl phthalate to enable reactions that cannot proceed under unactivated conditions. The activation by adding phthalate was ligand- and solvent-dependent, and it was unique to dipimp and N-methyl-2-pyrrolidone (NMP). With use of diphosphine ligand instead of dipimp or with use of tetrahydrofuran (THF) instead of NMP, no activation by a phthalate additive was observed. This simple method of catalyst activation with use of inexpensive, commercially available compounds is highly practical and may find many applications.
Key words
cycloaddition - homogeneous catalysis - alkynes - esters - ligands - phthalate - catalyst activationSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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Recent examples:
To date, synthesis of 4,5,6,7-tetraalkyl 2,3-dihydro-1H-indenes by catalytic cycloaddition of the corresponding 1,6-diyne and an aliphatic internal alkyne could only be found in the following three reports:
Effective non-Cp catalysts for fully intermolecular cyclotrimerizations of internal aliphatic alkynes: [Co]
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