Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 48, Pages 15309-15313Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201707958
Keywords
C-H alkylation; DFT studies; manganese; Minisci reaction; redox chemistry
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Funding
- Pfizer Inc.
- Natural Sciences and Engineering Research Council (NSERC)
- Fonds de Recherche du Quebec en Sciences et Technologies (FRQNT)
- Canadian Foundation for Innovation (CFI)
- NanoQAM
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A visible-light-driven Minisci protocol that employs an inexpensive earth-abundant metal catalyst, decacarbonyldimanganese Mn-2(CO)(10), to generate alkyl radicals from alkyl iodides has been developed. This Minisci protocol is compatible with a wide array of sensitive functional groups, including oxetanes, sugar moieties, azetidines, tert-butyl carbamates (Boc-group), cyclobutanes, and spirocycles. The robustness of this protocol is demonstrated on the late-stage functionalization of complex nitrogen-containing drugs. Photophysical and DFT studies indicate a light-initiated chain reaction mechanism propagated by Mn-.(CO)(5). The rate-limiting step is the iodine abstraction from an alkyl iodide by Mn-.(CO)(5).
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