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Photoredox Catalysis in Late-Stage Aryl C(sp3 )−H Functionalizations

Portrait of Patrick Foster, graduate student speaker
Patrick Foster
Graduate Student, Department of Chemistry
University of Georgia
iSTEM Building 2, Room 1218
Organic Seminar

The high prevalence of aromatics in natural products and potential drug candidates makes them intriguing candidates for continued development of C-H functionalization reactions that proceed with high positional selectivity. Achieving site-selectivity can be a steep challenge as when there is a lack of appropriate directing groups or substitution patterns, more than one product isomer is commonly produced. Therefore, the development of aromatic C-H functionalization by means of chemo and site-selective activation is of interest. 

The field of photoredox catalysis has continued to grow at a rapid rate due to the vast scope of synthetic transformations that are possible. Since the advent of photoredox catalysis, the development and application of light-induced reactions have brought about the creation of a variety of new bond constructions. In 1984, Cano-Yelo and Deronzier reported the first net oxidative photoredox-catalyzed reaction using aryldiazonium salts as the terminal oxidant for the conversion of benzylic alcohols to the corresponding aldehydes, shortly after this they disclosed the first redox-neutral transformation.1 Several years after, the vast utility of alkyl radicals was realized during the pioneering work of Okada and co-workers, when they reported photosensitized decarboxylative Michael Addition through N-(acyloxy)phthalimides.2 The field remained relatively inert until the late 2000s. In 2008, Yoon and co-workers disclosed a photoredox-catalyzed enone cycloadditon reaction, modulating the reactivity of enone substrate through use of a Lewis acid additive.3 Following this was the work done by MacMillan and co-workers using photoredox catalysis for the enantioselective alkylation of aldehydes.4 These reports underscored the applicability of photoredox catalysis as an efficient yet nontoxic means of activation. 

The merger of photoredox catalysis with other organocatalytic activation modes expanded the repertoire of C-C and C-H bond formations. Overall, the robust repertoire of photoredox catalysis as well as its application pertaining to aromatic C-H functionalizations will be discussed. 


[1]Cano-Yelo, H., Deronzier, A. Tetrahedron Lett. 1984, 25, 5517-5520. 

[2]Okada, K,. et al. J. Am. Chem. 1991, 113, 9401-9402. 

[3]Yoon, Juana., et al. J. Am. Chem. 2008, 130, 12886-18887. 

[4]MacMillan, D., et al. Science. 2008, 322, 77-80. 

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