Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 10, Pages 1453-1458Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900786
Keywords
Photoredox; Photocatalysis; Heterocycles; Alkylation; Redox-neutral
Categories
Funding
- Natural Sciences and Engineering Research Council (NSERC)
- University of Ottawa
- NSERC
- government of Ontario
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Radical additions to heteroaromatic bases are frequently employed for the rapid synthesis of complex products using C-H functionalization strategies. The conditions that are commonly employed are typically harsh, routinely requiring stoichiometric oxidants and other additives. In search for milder reaction environments allowing late-stage functionalization, we present the alkylation of N-heteroarenes using primary alcohols and ethers as radical precursors, where the corresponding alkyl radical is formed via hydrogen atom transfer process with a photoredox catalyzed chlorine atom generation as HAT agent. Furthermore, we explore the reduction of the heteroarenes in moderate to high yields when using secondary alcohols.
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