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Enantioselective Ring-Opening/Oxidative Phosphorylation and P‑Transfer Reaction of Cyclic Diaryliodoniums

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posted on 2019-10-02, 15:05 authored by Longhui Duan, Kun Zhao, Zhonggui Wang, Feng-Lian Zhang, Zhenhua Gu
A Cu-catalyzed enantioselective ring-opening/oxidative phosphorylation reaction of cyclic diaryliodonium salts and diarylphosphine oxides in the presence of TEMPO was reported. 18O-Labeled experiments showed that the reaction proceeded via oxidation, followed by C–O bond formation. Furthermore, atropisomeric phosphine oxides were prepared via a t-BuLi-mediated P-transfer reaction. Computational studies elucidated that the phosphine oxide transfer was through a concerted C–P bond formation and P–O bond-dissociation process.

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