EDA Photochemistry: Mechanistic Investigations and Future Opportunities
Authors
Affiliations
Recently, organic synthesis has seen a renaissance in radical chemistry due to the accessibility of mild methods for radical generation using visible light. While renewed interest in synthetic radical chemistry has been driven by the advent of photoredox catalysis, a resurgence of electron donor-acceptor (EDA) photochemistry has also led to many new radical transformations. Similar to photoredox catalysis, EDA photochemistry involves light-promoted single-electron transfer pathways. However, the mechanism of electron transfer in EDA systems is unique wherein the lifetimes of radical intermediates are often shorter due to competitive back-electron transfer. Distinguishing between EDA and photoredox mechanisms can be challenging since they can form identical products. In this perspective, we seek to provide insight on the mechanistic studies which can distinguish between EDA and photoredox manifolds. Additionally, we highlight some key challenges in EDA photochemistry and suggest future goals which could advance the synthetic potential of this field of research.
Lai Z, Xie Y, Huang L, Guo J, Lu G Chem Sci. 2025; 16(10):4352-4359.
PMID: 39911333 PMC: 11793018. DOI: 10.1039/d4sc07264b.
Giese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation.
van der Heide P, Retini M, Fanini F, Piersanti G, Secci F, Mazzarella D Beilstein J Org Chem. 2024; 20:3274-3280.
PMID: 39717264 PMC: 11665442. DOI: 10.3762/bjoc.20.271.
Light-Mediated Direct Decarboxylative Giese Aroylations without a Photocatalyst.
Kitcatt D, Pogacar E, Mi L, Nicolle S, Lee A J Org Chem. 2024; 89(21):16055-16059.
PMID: 39438444 PMC: 11536358. DOI: 10.1021/acs.joc.4c02163.
Farcas A, Bende A Int J Mol Sci. 2024; 25(19).
PMID: 39408851 PMC: 11477014. DOI: 10.3390/ijms251910522.
Visible light-induced chemoselective 1,2-diheteroarylation of alkenes.
Guo S, Liu Y, Huang J, He L, He G, Ji D Nat Commun. 2024; 15(1):6102.
PMID: 39030211 PMC: 11271625. DOI: 10.1038/s41467-024-50460-4.