Ruthenium-catalyzed regioselective [2 + 2 + 2] cyclotrimerization of trifluoromethyl group substituted internal alkynes

Motoi Kawatsura; Mitsuaki Yamamoto; Junya Namioka; Koji Kajita; Takuya Hirakawa; Toshiyuki Itoh

doi:10.1021/ol1030734

Ruthenium-catalyzed regioselective [2 + 2 + 2] cyclotrimerization of trifluoromethyl group substituted internal alkynes

Org Lett. 2011 Mar 4;13(5):1001-3. doi: 10.1021/ol1030734. Epub 2011 Feb 2.

Authors

Motoi Kawatsura¹, Mitsuaki Yamamoto, Junya Namioka, Koji Kajita, Takuya Hirakawa, Toshiyuki Itoh

Affiliation

¹ Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, Koyama, Tottori, Japan. kawatsur@chem.tottori-u.ac.jp

PMID: 21288010
DOI: 10.1021/ol1030734

Abstract

It found that the Ru(3)(CO)(12) coordinated with 2-(diphenylphosphino)benzonitrile (2-DPPBN) to effectively catalyze the [2 + 2 + 2] cyclotrimerization of the trifluoromethyl group substituted internal alkynes in high yields with up to >98% regioselectivity. Isolation of a ruthenacyclopentadiene was successful and confirmed that the complex is a reaction intermediate.

MeSH terms

Alkynes / chemistry*
Catalysis
Crystallography, X-Ray
Cyclization
Fluorobenzenes / chemical synthesis*
Fluorobenzenes / chemistry
Hydrocarbons, Fluorinated / chemical synthesis*
Hydrocarbons, Fluorinated / chemistry*
Molecular Structure
Nitriles / chemistry*
Phosphines / chemistry*
Ruthenium / chemistry*
Stereoisomerism

Substances

2-(diphenylphosphino)benzonitrile
Alkynes
Fluorobenzenes
Hydrocarbons, Fluorinated
Nitriles
Phosphines
Ruthenium