Benchtop-Stable Hypervalent Bromine(III) Compounds: Versatile Strategy and Platform for Air- and Moisture-Stable λ3‑Bromanes

Benchtop-Stable Hypervalent Bromine(III) Compounds: Versatile Strategy and Platform for Air- and Moisture-Stable λ3‑Bromanes

We present the first synthesis of air/moisture-stable λ3-bromanes (9 and 10) by using a cyclic 1,2-benzbromoxol-3-one (BBX) strategy. X-ray crystallography and NMR and IR spectroscopy of N-triflylimino-λ3-bromane (12) revealed that the bromine­(III) center is effectively stabilized by intramolecular...

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Veröffentlicht in:Journal of the American Chemical Society 2021-06, Vol.143 (25), p.9327-9331
Hauptverfasser: Miyamoto, Kazunori, Saito, Motomichi, Tsuji, Shunsuke, Takagi, Taisei, Shiro, Motoo, Uchiyama, Masanobu, Ochiai, Masahito
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Sprache:eng
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Zusammenfassung:We present the first synthesis of air/moisture-stable λ3-bromanes (9 and 10) by using a cyclic 1,2-benzbromoxol-3-one (BBX) strategy. X-ray crystallography and NMR and IR spectroscopy of N-triflylimino-λ3-bromane (12) revealed that the bromine­(III) center is effectively stabilized by intramolecular R–Br–O hypervalent bonding. This strategy enables the synthesis of a variety of air-, moisture-, and benchtop-stable Br-hydroxy, -acetoxy, -alkynyl, -aryl, and bis­[(trifluoromethyl)­sulfonyl]­methylide λ3-bromane derivatives.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c04536