Highly selective and practical hydrogenation of functionalized (hetero)arenes

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. Diastereoselective hydrogenation of multi-substituted (hetero)arenes provides an efficient and industrially valuable route for transforming these compounds into diversified 3D building blocks, with broad applications such as drug discovery. Here, the authors demonstrate that a rationally designed Pt catalyst enables general diastereoselective hydrogenation of a wide variety of multi-substituted and functionalized arenes and heteroarenes under mild conditions.