Carbon-Caron (C-C) coupling reactions have been conventionally carried out using homogeneous palladium (Pd) based catalysts. Recently, metal and metal-oxide nanoparticle-based heterogeneous catalysts have emerged as attractive catalysts for these reactions. However, identification of the catalytic pathway remains a challenge in the field. In this contribution, we show that by choosing appropriate reaction conditions, the reaction pathway can be controlled to occur via a truly homogeneous or heterogeneous pathway in cuprous oxide (Cu2O)-nanoparticle-catalyzed C-C coupling reactions. When the reactions are carried out in the liquid phase using dimethylformamide as the solvent, the surface atoms of Cu2O nanoparticles undergo leaching and form homogenous Cu complex in the presence of the base. The in-situ formed homogenous Cu complexes can successfully catalyze (i) oxidative C-C homo-coupling of terminal alkynes, and (ii) C-C cross-coupling reactions between aryl halides and terminal alkyne. In contrast, when the reactions are performed in the absence of base, the C-C coupling reactions occur truly via a heterogeneous pathway. The molecular reaction mechanisms are proposed for both homogeneous and heterogeneous pathways. The mechanistic understanding from this work has the potential for the development of (a) an inexpensive Cu-based catalyst as a suitable replacement for expensive Pd based catalysts, and (b) a heterogeneous catalyst capable of exhibiting long term stability to develop energy-efficient and environmentally friendly flow processes.

Heterogeneously catalyzed C-C coupling reactions using earth-abundant cuprous oxide nanoparticles in condensed phase

Macromolecular Chemistry: The Second Century

[Author Benefits](https://scimeetings.acs.org/?utm_source=pubs_content_marketing&utm_medium=website&utm_campaign=0320_MCF_NPI_Launch_Spring_Homepage&ref=pubs_content_marketing)

[How to use SciMeetings](https://storage.googleapis.com/dl.morressier.com/acs/SciMeetings-ACSSpring2020-HowToGuide_M3020-Final.pdf)

[Frequently Asked Questions](https://storage.googleapis.com/dl.morressier.com/acs/SciMtng_ACSNMSp2020_FAQ_M3120_Final.pdf)

ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.