Synlett 2012; 23(17): 2549-2553
DOI: 10.1055/s-0032-1317318
letter
© Georg Thieme Verlag Stuttgart · New York

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: [email protected]
,
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: [email protected]
,
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: [email protected]
,
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: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 25 July 2012

Accepted after revision: 27 August 2012

Publication Date:
28 September 2012 (online)


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.

Supporting Information

 
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