Arenophile-Mediated Photochemical Dearomatization of Nonactivated Arenes

Authors

  • Mikiko Okumura Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA
  • David Sarlah Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA; Dipartimento di Chimica Organica, Università di Pavia, V. le Taramelli 12, 27100 Pavia, Italy;, Email: sarlah@illinois.edu

DOI:

https://doi.org/10.2533/chimia.2020.577

Keywords:

Arenophile, Catalysis, Dearomatization, Functionalization, Natural products

Abstract

Aromatic compounds are one of the most abundant classes of organic molecules and find utility as precursors for alicyclic hydrocarbon building blocks. While many established dearomatization reactions are exceptionally powerful, dearomatization with concurrent introduction of functionality, i.e. dearomative functionalization, is still a largely underdeveloped field. This review aims to provide an overview of our recent efforts and progress in the development of dearomative functionalization of simple and nonactivated arenes using arenophile-arene cycloaddition platform. These cycloadducts, formed via a visible-light-mediated [4+2]-photocycloaddition, can be elaborated in situ through olefin chemistry or transition-metal-catalyzed ring-opening with carbon-, nitrogen-, and oxygen-based nucleophiles, providing access to diverse structures with functional and stereochemical complexity. Moreover, the dearomatized products are amenable to further elaborations, which effectively install other functionalities onto the resulting alicyclic carbocycles. The utility of the arenophile-mediated dearomatization methods are also highlighted by the facile syntheses of natural products and bioactive compounds through novel disconnections.

Downloads

Published

2020-08-12

How to Cite

[1]
M. Okumura, D. Sarlah, Chimia 2020, 74, 577, DOI: 10.2533/chimia.2020.577.