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Synthesis of 2,3-dihydro-1H-phosphindole-1-oxides via the t-BuLi-mediated rearrangement of vinyl bromides and phosphine oxides

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Abstract

We report an intramolecular addition reaction of vinyllithium to phosphine oxides for the efficient synthesis of 2,3-dihydro-1H-phosphindole-1-oxides. Control experiments indicated that the reaction might proceed through an addition and concerted aryl migration process. The relative migration rate of aryl rings with different electronic properties was also briefly investigated.

Graphical abstract: Synthesis of 2,3-dihydro-1H-phosphindole-1-oxides via the t-BuLi-mediated rearrangement of vinyl bromides and phosphine oxides

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Publication details

The article was received on 20 Apr 2017, accepted on 17 Jun 2017 and first published on 20 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QO00310B
Citation: Org. Chem. Front., 2017, Advance Article
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    Synthesis of 2,3-dihydro-1H-phosphindole-1-oxides via the t-BuLi-mediated rearrangement of vinyl bromides and phosphine oxides

    B. Li, M. Zhang, X. Huang and Z. Gu, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00310B

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