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JACS Au. 2025 Jan 8;5(1):99-110. doi: 10.1021/jacsau.4c00809 Q18.72025

Merging Copper Catalysis with Nitro Allyl and Allyl Sulfone Derivatives: Practical, Straightforward, and Scalable Synthesis of Diversely Functionalized Allyl Boranes

铜催化与硝基亚基和亚基砜衍生物的结合:多功能化亚基硼烷的实用,简便和可放大的合成方法 翻译改进

Nicolas Fincias  1, Louis Clavier  1, Cora Escande de Messières  1, Marianne Guillard  1, Mansour Dole Kerim  1, Nicolas Casaretto  2, Julian Garrec  3, Stellios Arseniyadis  4, Laurent El Kaïm  1

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作者单位

  • 1 Laboratoire de Synthèse Organique (LSO-UMR 7652) CNRS, Ecole Polytechnique, ENSTA-Paris, Institut Polytechnique de Paris 828 Bd des Maréchaux, 91128 Palaiseau Cedex, France.
  • 2 Laboratoire de Chimie Moléculaire (LCM-UMR 9168) CNRS, Ecole Polytechnique, Institut Polytechnique de Paris, 91128 Palaiseau, France.
  • 3 Unité Chimie et Procédés (UCP) ENSTA-Paris, Institut Polytechnique de Paris, 828 Bd des Maréchaux, 91128 Palaiseau Cedex, France.
  • 4 Queen Mary University of London, Department of Chemistry, Mile End Road, London E1 4NS, U.K.
  • DOI: 10.1021/jacsau.4c00809 PMID: 39886564

    摘要 Ai翻译

    We report here the first example of a copper-catalyzed transformation involving nitro allyl derivatives. This borylation reaction, which exploits the high versatility of the aforementioned precursor, tolerates a variety of functional groups and allows practical, scalable, and highly straightforward access to diversely substituted allylboronic esters in high yields. The method was also extended to allyl sulfones, which provides a very complementary approach, offering additional structural diversity along with improved stereoselectivities. This new reactivity was further exploited to synthesize γ-fluoroallyl boronic esters as well as various synthetically useful building blocks through key post-functionalizations. Both the reaction mechanism and the chemoselectivity were rationalized experimentally and through DFT calculations.

    Keywords:copper catalysis; nitro allyl; sulfone derivatives; functionalized allyl boranes

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    期刊名:Jacs au

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    ISSN:N/A

    e-ISSN:2691-3704

    IF/分区:8.7/Q1

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    Merging Copper Catalysis with Nitro Allyl and Allyl Sulfone Derivatives: Practical, Straightforward, and Scalable Synthesis of Diversely Functionalized Allyl Boranes