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

Katsumasa Fujiki; Katsunori Tanaka

doi:10.1055/s-0036-1590956

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(05): 1097-1104
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

Katsumasa Fujiki

^aBiofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan eMail: kotzenori@riken.jp

,

Katsunori Tanaka*

^aBiofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan eMail: kotzenori@riken.jp

^bBiofunctional Chemistry Laboratory, Alexandar Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, Kazan 420008, Russian Federation

^cJST-PRESTO, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan

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Abstract

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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 activation

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