Silica nanospheres supported diazafluorene iron complex: an efficient and versatile nanocatalyst for the synthesis of propargylamines from terminal alkynes, dihalomethane and amines

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Abstract

A novel silica nanosperes supported diazafluorene iron complex has been fabricated and found to be effective in three-component coupling reaction of terminal alkynes, dichloromethane and amines.

Abstract

We present the synthesis of an efficient heterogeneous silica nanosphere supported iron catalyst (SiO ₂@APTES@DAFO-Fe) and its catalytic application in a one pot three-component coupling reaction of terminal alkynes, dihalomethane and secondary amines for the facile synthesis of propargylamines. The synthesized SiO ₂@APTES@DAFO-Fe nanocatalyst has been systematically characterized by solid-state ¹³C CPMAS and ²⁹Si CPMAS NMR spectroscopy, fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), Brunauer–Emmett–Teller (BET) surface area analysis, scanning electron microscopy (SEM), atomic absorption spectroscopy (AAS), energy dispersive X-ray fluorescence spectroscopy (ED-XRF), and elemental analysis. The nanocatalyst exhibits high catalytic performance for the coupling reaction of aromatic terminal alkynes, dichloromethane and secondary amines to afford propargylamines. In order to achieve high catalytic efficacy, the effect of various reaction parameters such as temperature, base, the amount of catalyst, reaction time, type of solvent, substrate molar ratio etc. have been investigated. Furthermore, the recovery and reuse of the quasi-homogeneous nano-catalyst have been demonstrated several times without any appreciable loss in its catalytic activity. Apart from this, FT-IR, SEM and HRTEM techniques are employed in order to prove the stability of the reused nano-catalyst. The present protocol works under mild reaction conditions with the additional advantages of a simple work-up procedure, high product yield, and easy recovery and reusability of the nanostructured catalyst. It is noteworthy that this atom economical methodology does not require an additional co-catalyst or activator. A tentative mechanism is also proposed for the one pot coupling reaction for the synthesis of propargylamines.

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Transition Metal Catalyzed Coupling Reactions under C−H Activation

Gerald Dyker (1999)

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Towards multifunctional, targeted drug delivery systems using mesoporous silica nanoparticles--opportunities & challenges.

Cecilia Sahlgren, Jessica M Rosenholm, Hannah Linden (2010)

One of the big challenges of medicine today is to deliver drugs specifically to defected cells. Nanoparticulate drug carriers have the potential to answer to this call, as nanoparticles can cross physiological barriers and access different tissues, and also be provided in a targetable form aimed at enhancing cell specificity of the carrier. Recent developments within material science and strong collaborative efforts crossing disciplinary borders have highlighted the potential of mesoporous silica nanoparticles (MSNs) for such targeted drug delivery. Here we outline recent advances which in this sense push MSNs to the forefront of drug delivery development. Relatively straightforward inside-out tuning of the vehicles, high flexibility, and potential for sophisticated release mechanisms make these nanostructures promising candidates for targeted drug delivery such as 'smart' cancer therapies. Moreover, due to the large surface area and the controllable surface functionality of MSNs, they can be controllably loaded with large amounts of drugs and coupled to homing molecules to facilitate active targeting, simultaneously carrying traceable (fluorescent or magnetically active) modalities, also making them highly interesting as theragnostic agents. However, the increased relative surface area and small size, and flexible surface functionalization which is beneficially exploited in nanomedicine, consequently also includes potential risks in their interactions with biological systems. Therefore, we also discuss some safety issues regarding MSNs and highlight how different features of the drug delivery platform influence their behaviour in a biological setting. Addressing these burning questions will facilitate the application of MSNs in nanomedicine.