Late-Stage Functionalization of Arylacetic Acids by Photoredox-Catalyzed Decarboxylative Carbon-Heteroatom Bond Formation.
Yota SakakibaraEri ItoTomohiro FukushimaKei MurakamiKenichiro ItamiPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2018)
The rapid transformation of pharmaceuticals and agrochemicals enables access to unexplored chemical space and thus has accelerated the discovery of novel bioactive molecules. Because arylacetic acids are regarded as key structures in bioactive compounds, new transformations of these structures could contribute to drug/agrochemical discovery and chemical biology. This work reports carbon-nitrogen and carbon-oxygen bond formation through the photoredox-catalyzed decarboxylation of arylacetic acids. The reaction shows good functional group compatibility without pre-activation of the nitrogen- or oxygen-based coupling partners. Under similar reaction conditions, carbon-chlorine bond formation was also feasible. This efficient derivatization of arylacetic acids makes it possible to synthesize pharmaceutical analogues and bioconjugates of pharmaceuticals and natural products.
Keyphrases
- room temperature
- small molecule
- visible light
- electron transfer
- high resolution
- high throughput
- ms ms
- drinking water
- emergency department
- hepatitis c virus
- adverse drug
- simultaneous determination
- gas chromatography mass spectrometry
- transition metal
- high performance liquid chromatography
- single cell
- liquid chromatography
- antiretroviral therapy
- sensitive detection
- tissue engineering