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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2020, 22, 6, 2303-2307
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Reductive Difunctionalization of Aryl Alkenes with Sodium Metal and Reduction-Resistant Alkoxy-Substituted Electrophiles

Cite this: Org. Lett. 2020, 22, 6, 2303–2307
Publication Date (Web):March 3, 2020
https://doi.org/10.1021/acs.orglett.0c00490
Copyright © 2020 American Chemical Society
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Abstract

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A general method for alkali-metal-promoted reductive difunctionalization of alkenes has been developed by means of reduction-resistant alkoxy-substituted electrophiles. A series of 1,2-diboration and 1,2-dicarbofunctionalization products can be synthesized by employing trimethoxyborane and strained cyclic ethers such as oxirane and oxetane. In addition, unsymmetrical carbo- or thioborations have been accomplished via sequential treatment with trimethoxyborane and carbon or sulfur electrophiles.

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  • Experimental procedures, X-ray crystallographic analysis, and spectral data (PDF)

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Cited By

This article is cited by 3 publications.

  1. Russell F. Snead, Jan Nekvinda, Webster L. Santos. Copper( ii )-catalyzed protoboration of allenes in aqueous media and open air. New Journal of Chemistry 2021, 5 https://doi.org/10.1039/D0NJ02010A
  2. Hideki Yorimitsu. Electron injection for aromatic metamorphosis of indole. Journal of the Chinese Chemical Society 2020, https://doi.org/10.1002/jccs.202000369
  3. Kanak Kanti Das, Swagata Paul, Santanu Panda. Transition metal-free synthesis of alkyl pinacol boronates. Organic & Biomolecular Chemistry 2020, 18 (44) , 8939-8974. https://doi.org/10.1039/D0OB01721C

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