Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 37, Pages 20237-20242Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202106531
Keywords
allylation; CF2-bridged 1; 5-diene; Cope rearrangement; selective C-F bond functionalization; trifluoromethylalkene
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Funding
- National Natural Science Foundation of China [21801131, 21871138]
- Thousand Talents Plan Youth Program
- Jiangsu Specially-Appointed Professor Plan
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This study presents a novel protocol for the C-F bond elaboration of trifluoromethylalkene derivatives, allowing for the expedient construction of structurally diversified CF2-bridged 1,5-dienes with exquisite selectivity based on a cascade of nucleophilic S(N)2 ' defluorinative allylation and electronically promoted Cope rearrangement.
Selective C-F bond functionalization of CF3 group represents an appealing strategy for the incorporation of pharmaceutically privileged difluoromethylene moiety. Despite the recent significant advancement attained in the functionalization of Ar-CF3 molecules, prescriptions amenable for alkenyl-CF3 congeners remain sufficiently inadequate. Herein, we report a strategically novel protocol for the C-F bond elaboration of trifluoromethylalkene derivatives. By using readily available allyl metallics as nucleophilic coupling partner, the present reaction enables an expedient construction of structurally diversified CF2-bridged 1,5-dienes. Furthermore, the exquisite selectivity observed in this transformation is revealed to be based on the underlying mechanism that consists of a cascade of nucleophilic S(N)2 ' defluorinative allylation and electronically promoted Cope rearrangement.
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