Selective Arene Hydrogenation for Direct Access to Saturated Carbo- and Heterocycles

Mario P. Wiesenfeldt, Zackaria Nairoukh, Toryn Dalton, Frank Glorius*

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

168 Scopus citations

Abstract

Arene hydrogenation provides direct access to saturated carbo- and heterocycles and thus its strategic application may be used to shorten synthetic routes. This powerful transformation is widely applied in industry and is expected to facilitate major breakthroughs in the applied sciences. The ability to overcome aromaticity while controlling diastereo-, enantio-, and chemoselectivity is central to the use of hydrogenation in the preparation of complex molecules. In general, the hydrogenation of multisubstituted arenes yields predominantly the cis isomer. Enantiocontrol is imparted by chiral auxiliaries, Brønsted acids, or transition-metal catalysts. Recent studies have demonstrated that highly chemoselective transformations are possible. Such methods and the underlying strategies are reviewed herein, with an emphasis on synthetically useful examples that employ readily available catalysts.

Original languageAmerican English
Pages (from-to)10460-10476
Number of pages17
JournalAngewandte Chemie - International Edition
Volume58
Issue number31
DOIs
StatePublished - 29 Jul 2019
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Keywords

  • arene hydrogenation
  • chemoselectivity
  • cycloalkanes
  • heterocycles
  • stereoselectivity

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