Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 7, Pages 2139-2143Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201813356
Keywords
1; 5-HAT; alkoxy radical; C-H activation; dual catalysis; photoredox catalyst
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Funding
- EPFL (Switzerland)
- Swiss National Science Foundation (SNSF) [200021-178846/1]
- Swiss National Science Foundation (SNF) [200021_178846] Funding Source: Swiss National Science Foundation (SNF)
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Under mild dual photoredox/copper catalysis, the reaction of N-alkoxypyridinium salts with readily available silyl reagents (TMSN3, TMSCN, TMSNCS) afforded -azido, -cyano, and -thiocyanato alcohols in high yields. The reaction went through a domino process involving alkoxy radical generation, 1,5-hydrogen atom transfer (1,5-HAT) and copper-catalyzed functionalization of the resulting C-centered radical. Conditions for catalytic enantioselective -C(sp(3))-H cyanation were also documented.
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