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Autocatalytic alkyne cycloadditions: evidence for colloidal Pt catalysis
Rowshan Ara Begum1, Nripen Chanda, T V V Ramakrishna
1Department of Chemistry, University of Missouri, 125 Chemistry Building, Columbia, Missouri 65211, USA.
Platinum-containing compounds react with diphenylacetylene to form new polycyclic aromatic hydrocarbons. Colloidal platinum, generated in situ, catalyzes these coupling reactions, accelerating the process.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Synthetic Organic Chemistry
Background:
- Four-membered and five-membered platinacycles are organometallic compounds containing platinum.
- These compounds can undergo reactions with alkynes, leading to the formation of new carbon-carbon bonds.
Purpose of the Study:
- To investigate the reaction of platinacycles with diphenylacetylene.
- To identify the products of these reactions and understand the reaction mechanism, including any catalytic effects.
Main Methods:
- Treatment of platinacycles (L2Pt(1,8-naphthalendiyl) and L2Pt(1,12-triphenylendiyl)) with excess diphenylacetylene (PhCCPh) at elevated temperatures (120-150°C).
- Analysis of reaction products using spectroscopic and analytical techniques.
- Investigation of reaction kinetics and identification of catalytic species.
Main Results:
- Formation of coupling products: 1,2-diphenylacenaphthalene and 4,5-diphenylbenzo[e]pyrene.
- Isolation of an alkyne complex, L2Pt(eta2-PhCCPh), as a byproduct.
- Observation of accelerating reaction rates attributed to colloidal platinum catalysis.
Conclusions:
- Platinacycles react with diphenylacetylene to yield polycyclic aromatic hydrocarbons and alkyne complexes.
- The reaction is autocatalytic, facilitated by colloidal platinum formed during the reaction.
- This study elucidates a novel synthetic route and highlights the role of platinum nanoparticles in catalysis.
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