Ruthenium-catalyzed [2 + 2+ 2] cycloaddition of three different alkynes

A chemoselective [2 + 2 + 2] cycloaddition of an internal alkyne, a terminal alkyne and dimethyl acetylenedicarboxylate was efficiently catalyzed by Cp *RuCl(cod) to give trisubstituted o-phthalates in good yield. ▪ A chemoselective [2 + 2 + 2] cycloaddition of an internal alkyne, a terminal alkyne...

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Bibliographic Details
Published in:Journal of molecular catalysis. A, Chemical Chemical, 2005-09, Vol.239 (1), p.166-171
Main Authors: Ura, Yasuyuki, Sato, Yoshitaka, Tsujita, Hiroshi, Kondo, Teruyuki, Imachi, Misako, Mitsudo, Take-aki
Format: Article
Language:English
Subjects:
[2 + 2 + 2] Cycloaddition
Alkynes
Catalysis
Chemistry
Exact sciences and technology
General and physical chemistry
Molar ratio
o-Phthalates
Ruthenium
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:A chemoselective [2 + 2 + 2] cycloaddition of an internal alkyne, a terminal alkyne and dimethyl acetylenedicarboxylate was efficiently catalyzed by Cp *RuCl(cod) to give trisubstituted o-phthalates in good yield. ▪ A chemoselective [2 + 2 + 2] cycloaddition of an internal alkyne, a terminal alkyne and dimethyl acetylenedicarboxylate was efficiently catalyzed by Cp *RuCl(cod) to give trisubstituted o-phthalates in good yield. It is critical to control the molar ratio of the three substrates to achieve high chemoselectivity, and regioselectivity of the products is sensitively influenced by the bulkiness of substituents on the internal alkyne.
ISSN:1381-1169
1873-314X
DOI:10.1016/j.molcata.2005.06.009