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Synthesis 2018; 50(05): 1097-1104
DOI: 10.1055/s-0036-1590956
DOI: 10.1055/s-0036-1590956
paper
Bis[N,N′-(2-indanolyl)]-1,5-diazacyclooctane as Unique Metal Ligand: Self-Assembly of Palladium Nanoparticles and Catalytic Reactivity on C–C Bond Formation
This work was supported by the JSPS KAKENHI Grant Numbers JP16H03287, JP16K13104, and JP15H05843 as part of the Middle Molecular Strategy, and by RIKEN Incentive Research Projects 2016. This work was also performed with the support of the Russian Government Program for Competitive Growth, granted to the Kazan Federal University.Further Information
Publication History
Received: 08 September 2017
Accepted after revision: 17 October 2017
Publication Date:
13 November 2017 (online)
Abstract
A previously unreported 1,5-diazacyclooctane-palladium(II) complex was synthesized using bis[N,N′-(2-indanolyl)]-1,5-diazacyclooctane, which was readily prepared via a novel [4+4] homocyclization of the unsaturated imine intermediate generated from acrolein and 1-amino-2-indanol. Interestingly, the 1,5-diazacyclooctane-palladium(II) complex self-assembled to form palladium nanoparticles. This approach readily provided palladium nanoparticles simply by heating a mixture of palladium(II) acetate and bis[N,N′-(2-indanolyl)]-1,4-diazacyclooctane in dichloroethane at mild temperatures. The 1,5-diazacyclooctane-derivative-palladium nanoparticles were successfully deployed in synthetic applications as a heterogeneous catalyst, facilitating Suzuki coupling and a challenging C–C bond formation via C(sp3)–H activation under low catalyst loading conditions.
Key words
1,5-diazacyclooctane - palladium nanoparticles - heterogeneous catalyst - chiral ligand - Suzuki coupling - C(sp3)–H activationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590956.
- Supporting Information
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