Remarkable Activation of an Alkyne [2+2+2]-Cycloaddition Catalyst, 2-Iminomethylpyridine (dipimp)/CoCl2·6H2O/Zn, by a Phthalate Additive

Yu-ki Sugiyama; Takuma Kariwa; Tetsuya Sakurada; Sentaro Okamoto

doi:10.1055/s-0032-1317318

Synlett, Inhaltsverzeichnis

Synlett 2012; 23(17): 2549-2553
DOI: 10.1055/s-0032-1317318

letter

Remarkable Activation of an Alkyne [2+2+2]-Cycloaddition Catalyst, 2-Iminomethylpyridine (dipimp)/CoCl₂·6H₂O/Zn, by a Phthalate Additive

Yu-ki Sugiyama

Department of Material and Life Chemistry, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan Fax: +81(45)4139770 eMail: okamos10@kanagawa-u.ac.jp

,

Takuma Kariwa

Department of Material and Life Chemistry, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan Fax: +81(45)4139770 eMail: okamos10@kanagawa-u.ac.jp

,

Tetsuya Sakurada

Department of Material and Life Chemistry, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan Fax: +81(45)4139770 eMail: okamos10@kanagawa-u.ac.jp

,

Sentaro Okamoto*

Department of Material and Life Chemistry, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan Fax: +81(45)4139770 eMail: okamos10@kanagawa-u.ac.jp

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Abstract

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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 activation

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Referenzen

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