Next Article in Journal
Thermodynamic Properties and Reversible Hydrogenation of LiBH4–Mg2FeH6 Composite Materials
Next Article in Special Issue
Reactivity of Zinc Halide Complexes Containing Camphor-Derived Guanidine Ligands with Technical rac-Lactide
Previous Article in Journal / Special Issue
Mechanistic Implications for the Ni(I)-Catalyzed Kumada Cross-Coupling Reaction
Article Menu
Issue 4 (December) cover image

Export Article

Open AccessArticle
Inorganics 2017, 5(4), 80;

Ruthenium-Catalyzed Dimerization of 1,1-Diphenylpropargyl Alcohol to a Hydroxybenzocyclobutene and Related Reactions

Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1 E4-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan
Precursory Research for Embryonic Science and Technology (PRESTO), Japan Science and Technology Agency (JST), 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan
Author to whom correspondence should be addressed.
Received: 28 October 2017 / Revised: 14 November 2017 / Accepted: 14 November 2017 / Published: 16 November 2017
Full-Text   |   PDF [2985 KB, uploaded 16 November 2017]   |  


Propargyl alcohol is a useful synthon in synthetic organic chemistry. We found that the ruthenium(II) complex [Cp*RuCl(diene)] (Cp* = η5-C5Me5; diene = isoprene or 1,5-cyclooctadiene (cod)) catalyzes dimerization of 1,1-diphenylprop-2-yn-1-ol (1,1-diphenylpropargyl alcohol, 1a) at room temperature to afford an alkylidenebenzocyclobutenyl alcohol 2a quantitatively. Meanwhile, a stoichiometric reaction of the related hydrido complex [Cp*RuH(cod)] with 1a at 50 °C led to isolation of a ruthenocene derivative 4 bearing a cyclopentadienyl ring generated by dehydrogenative trimerization of 1a. Detailed structures of 2a and 4 were determined by X-ray crystallography. The reaction mechanisms for the formation of 2a and 4 were proposed. View Full-Text
Keywords: ruthenium; alkyne; propargyl alcohol; C–H cleavage; benzocyclobutene ruthenium; alkyne; propargyl alcohol; C–H cleavage; benzocyclobutene

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material


Share & Cite This Article

MDPI and ACS Style

Nguyen, H.N.; Tashima, N.; Ikariya, T.; Kuwata, S. Ruthenium-Catalyzed Dimerization of 1,1-Diphenylpropargyl Alcohol to a Hydroxybenzocyclobutene and Related Reactions. Inorganics 2017, 5, 80.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Inorganics EISSN 2304-6740 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top