<p>Arenes, and particularly heteroarenes are integral structural components of a variety of chemicals and represent a privileged class of bioactive compounds found in pharmaceuticals, agrochemicals and vitamins. Diastereoselective hydrogenation of multi-substituted (hetero)arenes offers an efficient and industrially relevant approach to convert these compounds into valuable, diversified 3D building blocks for applications for example in drug innovation. We show that a rationally designed Pt catalyst permits the general diastereoselective hydrogenation of a broad range of multi-substituted and functionalized arenes and heteroarenes using mild conditions. The corresponding cyclic products are obtained with very high diastereoselectivity (d.r. value up to 99/1). The practical applicability of this catalysis is illustrated by the straightforward preparation of a novel plasticizer on kg-scale under solvent-free conditions.</p>

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Highly selective and practical hydrogenation of functionalized (hetero)arenes

  • Ruiyang Qu,
  • Soumyashree Jena,
  • Lifeng Xiao,
  • Hui Yang,
  • Rongsheng Cai,
  • Stephan Bartling,
  • Hanan Atia,
  • Ralf Jackstell,
  • Robert Franke,
  • Kathrin Junge,
  • Haijun Jiao,
  • Graham J. Hutchings,
  • Matthias Beller

摘要

Arenes, and particularly heteroarenes are integral structural components of a variety of chemicals and represent a privileged class of bioactive compounds found in pharmaceuticals, agrochemicals and vitamins. Diastereoselective hydrogenation of multi-substituted (hetero)arenes offers an efficient and industrially relevant approach to convert these compounds into valuable, diversified 3D building blocks for applications for example in drug innovation. We show that a rationally designed Pt catalyst permits the general diastereoselective hydrogenation of a broad range of multi-substituted and functionalized arenes and heteroarenes using mild conditions. The corresponding cyclic products are obtained with very high diastereoselectivity (d.r. value up to 99/1). The practical applicability of this catalysis is illustrated by the straightforward preparation of a novel plasticizer on kg-scale under solvent-free conditions.