Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 24, Pages 16245-16253Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02848
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Funding
- National Key Research and Development Program of China [2017YFD0200900]
- National Natural Science Foundation of China [21732002, 21672117, 21772104, 31760527]
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We developed a protocol for photoredox-mediated Minisci C-H alkylation reactions of N-heteroarenes in which readily available tert-butyl peroxyacetate acts as a radical relay precursor to generate alkyl radicals from alkyl iodides. This mild protocol tolerated a broad range of functional groups and could therefore be used for late-stage functionalization of complex nitrogen-containing natural products and drugs. Remarkably, by adopting a polarity-reversal strategy, we accomplished reactions that brought together an electron-deficient radical, a heteroarene to add alkene by means of a three-component radical relay process.
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