Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 41, Pages 12619-12623Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201707171
Keywords
alkoxyl radicals; donor-acceptor complexes; Hantzsch ester; photocatalysis; radical reactions
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Funding
- National Natural Science Foundation of China [21472230, 21622207]
- National Basic Research Program of China [2014CB910304]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20020200]
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The alkoxyl radical is an essential and prevalent reactive intermediate for chemical and biological studies. Here we report the first donor-acceptor complex-enabled alkoxyl radical generation under metal-free reaction conditions induced by visible light. Hantzsch ester forms the key donor-acceptor complex with N-alkoxyl derivatives, which is elucidated by a series of spectrometry and mechanistic experiments. Selective C(sp(3))-C(sp(3)) bond cleavage and allylation/alkenylation is demonstrated for the first time using this photocatalyst-free approach with linear primary, secondary, and tertiary alkoxyl radicals.
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