Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 7, Pages 1881-1884Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609885
Keywords
1,5-H transfer; C-H functionalization; dihydro-2H-pyrrole; photoredox reactions; tetralone
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Funding
- European Research Council [307948]
- Swiss National Science Foundation [200020_ 146853]
- European Research Council (ERC) [307948] Funding Source: European Research Council (ERC)
- Swiss National Science Foundation (SNF) [200020_146853] Funding Source: Swiss National Science Foundation (SNF)
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A redox-neutral, light-mediated functionalization of unactivated C(sp(3))-H bonds via iminyl radicals is presented here. A 1,5-H transfer followed by the functionalization of a C(sp(2))-H bond takes place in aqueous media producing a variety of elaborated fused ketones. Mechanistic investigations have revealed 1,5-H transfer as the reversible, rate-determining step in this transformation. Divergent scaffolds are also accessible via C(sp(3))-N bond formation upon a careful choice of the reaction additives.
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