Affiliation:
1. Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, ON N1G 2W1, Canada.
Abstract
Commercially available ruthenium catalyst, Cp*RuCl(COD), was found to be active in catalyzing Bis-Homo-Diels-Alder [2+2+2] cycloaddition reactions between 1,5-cyclooctadiene and various alkynes giving moderate to good yields (35%–92%). The presence of electron donating groups, especially hydroxyl groups, greatly enhanced the reactivity of the alkyne moiety in the cycloaddition. The reaction was also found to be successful even in the presence of bulky substituents on the alkynes.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
5 articles.
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1. Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings;Chemical Reviews;2021-02-12
2. Ruthenium-Catalyzed [2 + 2] versus Homo Diels–Alder [2 + 2 + 2] Cycloadditions of Norbornadiene and Disubstituted Alkynes: A DFT Study;ACS Omega;2020-12-18
3. Reactions of an Aluminum(I) Reagent with 1,2-, 1,3-, and 1,5-Dienes: Dearomatization, Reversibility, and a Pericyclic Mechanism;Inorganic Chemistry;2020-03-24
4. Cationic Ruthenium-Catalyzed Bis-Homo-Diels-Alder Cycloaddition;Current Organic Synthesis;2019-10-17
5. Ruthenium-Catalyzed [2+2+2] Bis-Homo-Diels–Alder Cycloadditions of 1,5-Cyclooctadiene with Alkynyl Phosphonates;Synthesis;2019-08-21