Photocatalytic Alpha Arylation of Carbonyls

Case ID:

This invention is a method for the synthesis of alpha arylation of inexpensive, unactivated carbonyl compounds with high yields at room temperature using any photocatalyst (PC) under visible light from blue to red.

Functionalization of the C-H bond has evolved as a fundamental principle that underpins both academic and industrial importance in conceptualization and actualization of challenging organic transformations. This ubiquitous but relatively inert bond, if converted to more valuable C-C bond, can greatly accelerate the construction of a wide variety of compounds.  This transformation is particularly sought after in fine chemicals and pharmaceutical applications. Incorporation of an aryl substituents at the α-position of carbonyl compounds is a powerful and attractive method to construct a C(sp2)-C(sp3) bond; and its coupling products, especially α-aryl cyclic ketones are significant structural motifs that are often encountered in a wide range of biologically interesting natural and pharmaceutical products. A number of classical stoichiometric transformations have been employed for such a key transformation but suffered from complications in scale-up, either due to the need to use highly activated aryl halides as reactants or the use of stoichiometric amount of toxic reagents with harsh reaction conditions, e.g., a high reaction temperature. Significant efforts have been directed towards the development of alternative synthetic routes to this important scaffold. With the advances in metal-catalyzed transformations, palladium-catalyzed α-arylations of the carbonyl compounds appeared to be the most promising route due to its versatility. However, high cost of the catalyst and additives, as well as requiring a high reaction temperature limits the utility of this approach in the synthesis of α-aryl carbonyls as building block, especially for pharmaceutical applications.


  • Fine chemical synthesis
  • Synthesis of pharmaceutical intermediates or products
  • For example, isocoumarin compounds


  • Start from less expensive reactants
  • Wide variety of non-metal photocatalysts may be used
  • Room temperature synthesis
  • Environmentally friendly
  • One pot synthesis
Patent Information:
Contact For More Information:
Laura Silva
Sr. Licensing Manager, COS
The University of Arizona
Lead Inventor(s):
Thomas Gianetti
Md Mubarak Hossain