Highly selective and practical hydrogenation of functionalized (hetero)arenes
Ruiyang Qu1,2, Soumyashree Jena1, Lifeng Xiao3
1Leibniz-Institut für Katalyse e.V., Rostock, Germany.
A new platinum catalyst enables highly diastereoselective hydrogenation of arenes and heteroarenes. This efficient method creates valuable 3D building blocks for drug discovery and produces a plasticizer on a large scale.
Area of Science:
- Catalysis
- Organic Chemistry
- Materials Science
Background:
- Arenes and heteroarenes are crucial in pharmaceuticals, agrochemicals, and vitamins.
- Their conversion to 3D building blocks is vital for drug innovation.
- Diastereoselective hydrogenation is an efficient route for this transformation.
Purpose of the Study:
- To develop a catalyst for general diastereoselective hydrogenation of diverse arenes and heteroarenes.
- To achieve high diastereoselectivity under mild conditions.
- To demonstrate practical, large-scale applicability.
Main Methods:
- Rational design of a platinum (Pt) catalyst.
- Hydrogenation of multi-substituted and functionalized arenes and heteroarenes.
- Characterization of cyclic products for diastereoselectivity.
Main Results:
- The Pt catalyst facilitated general diastereoselective hydrogenation of a broad substrate scope.
- High diastereoselectivities (up to 99/1 d.r.) were achieved.
- A novel plasticizer was synthesized on a kg-scale under solvent-free conditions.
Conclusions:
- A rationally designed Pt catalyst enables efficient and highly diastereoselective hydrogenation of arenes and heteroarenes.
- This method provides valuable 3D building blocks for applications like drug innovation.
- The process is industrially relevant, demonstrated by scalable, solvent-free plasticizer synthesis.
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