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

Bin Li; Mingkai Zhang; Xulun Huang; Zhenhua Gu

doi:10.1039/C7QO00310B

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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†

Bin Li,^a Mingkai Zhang,^a Xulun Huang^a and Zhenhua Gu

*^a

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* Corresponding authors

^a Department of Chemistry and Hefei National Laboratory for Physical Sciences at the Microscale, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. China
E-mail: zhgu@ustc.edu.cn

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.

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DOI: https://doi.org/10.1039/C7QO00310B
Article type: Research Article
Submitted: 20 Apr 2017
Accepted: 17 Jun 2017
First published: 20 Jun 2017

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Org. Chem. Front., 2017,4, 1854-1857

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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, 4, 1854 DOI: 10.1039/C7QO00310B

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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†

Abstract

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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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