化学
药物化学
三键
试剂
双键
债券
戒指(化学)
区域选择性
作者
Chuan Zhu,Meng-Meng Sun,Kai Chen,Haidong Liu,Chao Feng
标识
DOI:10.1002/anie.202106531
摘要
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 SN 2' defluorinative allylation and electronically promoted Cope rearrangement.
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