Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 35, Pages 11413-11417Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201806434
Keywords
alkynylation; C-H functionalization; iron; radicals; reaction mechanisms
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Funding
- National Science Foundation of China [21722204, 21472112, 21432003]
- Fok Ying Tung Education Foundation [151035]
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An alkoxyl radical guided strategy for site-selective functionalization of unactivated methylene and methine C-H bonds enabled by an Fe-II-catalyzed redox process is described. The mild, expeditious, and modular protocol allows efficient remote aliphatic fluorination, chlorination, amination, and alkynylation of structurally and electronically varied primary, secondary, and tertiary hydroperoxides with excellent functional-group tolerance. The application for one-pot 1,4-hydroxyl functionalization of non-oxygenated alkane substrates initiated by aerobic C-H oxygenation is also demonstrated.
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