Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 21, Pages 5921-5925Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201701538
Keywords
amide activation; chemoselectivity; keteniminium ions; oxidative C-C coupling; umpolung
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Funding
- ERC (FLATOUT) [StG 278872]
- FWF [P27194]
- DFG
- University of Vienna
- DOC Fellowship of the Austrian Academy of Sciences
- Austrian Science Fund (FWF) [P27194] Funding Source: Austrian Science Fund (FWF)
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Much contemporary organic synthesis relies on transformations that are driven by the intrinsic, so-called natural, polarity of chemical bonds and reactive centers. The design of unconventionally polarized synthons is a highly desirable strategy, as it generally enables unprecedented retrosynthetic disconnections for the synthesis of complex substances. Whereas the umpolung of carbonyl centers is a well-known strategy, polarity reversal at the alpha-position of a carbonyl group is much rarer. Herein, we report the design of a novel electrophilic enolonium species and its application in efficient and chemoselective, metal-free oxidative C-C coupling.
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