Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 40, Pages 10794-10798Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406747
Keywords
alkynes; C-H activation; heterocycles; N-oxides; rhodium
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Funding
- NSFC [21272231]
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[Cp* Rh-III]-catalyzed C-H activation of arenes assisted by an oxidizing N-O or N-N directing group has allowed the construction of a number of hetercycles. In contrast, a polar N-O bond is well-known to undergo O-atom transfer (OAT) to alkynes. Despite the liability of N-O bonds in both C-H activation and OAT, these two important areas evolved separately. In this report, [Cp* Rh-III] catalysts integrate both areas in an efficient redox-neutral coupling of quinoline N-oxides with alkynes to afford alpha-(8-quinolyl) acetophenones. In this process the N-O bond acts as both a directing group for C-H activation and as an O-atom donor.
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