Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 10, Pages 7242-7255Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00573
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Funding
- SERB-DIA, India [DIA/2018/000034]
- SERB (DST), India [YSS/2014/000877]
- IISER-Kolkata
- CSIR
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This report presents a new method for hydrodehalogenation and dehalogenative deuteration of aryl/heteroaryl halides without the need for transition metals. The incorporation of deuterium into biologically active compounds was successfully achieved, and the mechanism was found to be based on single electron transfer through the combined approach of experimental and theoretical studies.
Dehalogenative deuteration reactions are generally performed through metal-mediated processes. This report demonstrates a mild protocol for hydrodehalogenation and dehalogenative deuteration of aryl/heteroaryl halides (39 examples) using a reduced odd alternant hydrocarbon phenalenyl under transition metal-free conditions and has been employed successfully for the incorporation of deuterium in various biologically active compounds. The combined approach of experimental and theoretical studies revealed a single electron transfer-based mechanism.
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