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'Radical' approach yields catalyst for sustainable indene synthesis

Date:
July 6, 2016
Source:
Universiteit van Amsterdam (UVA)
Summary:
A team of scientists has developed a new catalyst for the easy synthesis of substituted 1H-indenes. Based on the abundant element cobalt their cheap and easy to prepare catalytic complex is capable of the sustainable concept of metalloradical catalysis.
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Thermolysis of the applied tosyl hydrazones (easily prepared by condensation of the corresponding aldehydes with tosyl hydrazine) leads to in situ formation of the corresponding diazo compounds. The latter are activated by the catalyst, thus forming the key carbene-radical intermediates responsible for radical-type ring-closure to form the final indene products. The reaction has a broad substrate scope, tolerant to various different substituents, enabling facile synthesis of a variety of indene derivatives.
Credit: HIMS / Homkat

A team of scientists of the University of Amsterdam's research priority area Sustainable Chemistry has developed a new catalyst for the easy synthesis of substituted 1H-indenes. Based on the abundant element cobalt their cheap and easy to prepare catalytic complex is capable of the sustainable concept of metalloradical catalysis. Details have recently been published on the website of the Journal of the American Chemical Society.

Indenes are valuable building blocks of a variety of natural products, pharmaceuticals and other bio-active compounds. They also have widespread applications in metal complexes for catalytic use in e.g. olefin polymerization. As such, there is a demand for the development of fast, efficient and broadly applicable methods for indene synthesis from readily available starting materials.

The strategy now reported by the UvA's SusChem team contributes to this development by providing a sustainable catalytic route to indene synthesis. It resulted from their new, bio-inspired approach in the field of so-called metallo-radical catalysis. Here the intrinsic radical-type reactivity of first row transition metals is utilized, where most currently applied catalytic approaches are aimed at preventing radical formation.

According to research leader Bas de Bruin the concept of metallo-radical catalysis enables chemists to move away from the current use of expensive noble metal catalysts and use cheap metals instead. Inspired by the performance of natural metallo-enzymes, De Bruin and his co-workers at the UvA's research priority area Sustainable Chemistry are currently developing more future catalysts also based on the concept of radical reactivity.


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Materials provided by Universiteit van Amsterdam (UVA). Note: Content may be edited for style and length.


Journal Reference:

  1. Braja Gopal Das, Andrei Chirila, Moniek Tromp, Joost N. H. Reek, Bas de Bruin. CoIII-Carbene Radical Approach to Substituted 1H-Indenes. Journal of the American Chemical Society, 2016; DOI: 10.1021/jacs.6b05434

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Universiteit van Amsterdam (UVA). "'Radical' approach yields catalyst for sustainable indene synthesis." ScienceDaily. ScienceDaily, 6 July 2016. <www.sciencedaily.com/releases/2016/07/160706092803.htm>.
Universiteit van Amsterdam (UVA). (2016, July 6). 'Radical' approach yields catalyst for sustainable indene synthesis. ScienceDaily. Retrieved May 8, 2017 from www.sciencedaily.com/releases/2016/07/160706092803.htm
Universiteit van Amsterdam (UVA). "'Radical' approach yields catalyst for sustainable indene synthesis." ScienceDaily. www.sciencedaily.com/releases/2016/07/160706092803.htm (accessed May 8, 2017).