Journal
ORGANIC LETTERS
Volume 21, Issue 23, Pages 9719-9723Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03879
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Funding
- Institute for Basic Science [IBS-R010-A2]
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Visible-light-induced site-selective C(sp(3))-H pyridylation of amides has been accomplished using N-amidopyridinium salts. The N-centered radicals generated by the single-electron reduction of N-amidopyridinium substrates undergo 1,5-hydrogen atom transfer to form alkyl radical intermediates. Excellent C4-selectivity in radical trapping with pyridinium salts is observed for the alkyl radicals to provide delta-pyridyl sulfonamides and gamma-pyridyl carboxamides. The utility is demonstrated by offering a practical approach for the late-stage functionalization of complex amide derivatives.
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