Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 5, Pages 1872-1875Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510014
Keywords
allylic compounds; C-H functionalization; photochemistry; alkoxyl radicals; reaction mechanisms
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Funding
- National Basic Research Program of China [2014CB910304]
- National Natural Science Foundation of China [21272260, 21472230]
- Thousand Talents Program Young Investigator Award
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Reported herein is the first visible-light-induced formation of alkoxyl radicals from N-alkoxyphthalimides, and the Hantzsch ester as the reductant is crucial for the reaction. The selective hydrogen atom abstraction by the alkoxyl radical enables C(sp(3))-H allylation and alkenylation reactions under mild reaction conditions at room temperature. Broad substrate variations, including a structurally complexed steroid, undergo the C(sp(3))-H functionalization reaction effectively with high regio- and chemoselectivity.
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