Work

On-DNA hydroalkylation of N -vinyl heterocycles via photoinduced EDA-complex activation

Year: 2023

Type: article

Abstract: -vinyl heterocycles enabled by single-electron transfer (SET) and subsequent hydrogen atom transfer through electron-donor/electron-acceptor (EDA) complex activation is detailed. The simplicity and robustness of this method permits inclusion of a broad array of alkyl radical precursors and DNA-tethered nitrogenous heterocyles to generate medicinally relevant substituted heterocycles with pendant functional groups. Moreover, a successful telescoped route provides the opportunity to access a broad range of intricate structural scaffolds by employing basic carboxylic acid feedstocks.

Source: Chemical Science

DOI: 10.1039/d3sc03731b

Authors: Mohammed Sharique, Bianca Matsuo, Albert Granados, Saegun Kim, Mahwish Arshad, Hyunjung Oh, Victoria E. Wu, Minxue Huang, Adam Csakai, Lisa A. Marcaurelle, Gary A. Molander

Institutions: University of Pennsylvania, GlaxoSmithKline (United States)

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Science Foundation, University of Pennsylvania, National Institutes of Health, Vagelos Institute for Energy Science and Technology, University of Pennsylvania, National Institute of General Medical Sciences, Division of Chemistry

Awards: Computational Methods for Selective Catalysis, G2141756727, MRI: Acquisition of a 400 MHz Nuclear Magnetic Resonance (NMR) Spectrometer for Chemistry and Energy Research and Education at the University of Pennsylvania, G2989883016, G458626264, Targeting Nucleic Acid Junctions with Small Molecules, G7805455597, Accessing New Chemical Space via Organic Synthesis

OpenAlex ID: W4386751069

FWCI: 1.283

Cites: 47

Cited by: 13

Related to: 10