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Cobalt-catalyzed deoxygenative triborylation of allylic ethers to access 1,1,3-triborylalkanes

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  • Wei Jie Teo

    (National University of Singapore)

  • Xiaoxu Yang

    (National University of Singapore)

  • Yeng Yeng Poon

    (National University of Singapore)

  • Shaozhong Ge

    (National University of Singapore)

Abstract

Polyborylated organic compounds have been emerging as versatile building blocks in chemical synthesis. Here we report a selective cobalt-catalyzed deoxygenative 1,1,3-triborylation reaction of allylic ethers with pinacolborane to prepare 1,1,3-triborylalkane compounds. With naturally abundant and/or synthetic cinnamic methyl ethers as starting materials, we have achieved the synthesis of a variety of 1,1,3-triborylalkanes (25 examples). The synthetic utility of these 1,1,3-triborylalkanes is demonstrated through site-selective allylation, protodeborylation, and consecutive carbon-carbon bond-forming reactions. Mechanistic studies including deuterium-labeling and control experiments suggest that this 1,1,3-triborylation reaction proceeds through initial cobalt-catalyzed deoxygenative borylation of allylic ethers to form allylic boronates followed by cobalt-catalyzed 1,1-diborylation of the resulting allylic boronates.

Suggested Citation

  • Wei Jie Teo & Xiaoxu Yang & Yeng Yeng Poon & Shaozhong Ge, 2020. "Cobalt-catalyzed deoxygenative triborylation of allylic ethers to access 1,1,3-triborylalkanes," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
  • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-19039-7
    DOI: 10.1038/s41467-020-19039-7
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    Cited by:

    1. Shengnan Jin & Jinxia Li & Kang Liu & Wei-Yi Ding & Shuai Wang & Xiujuan Huang & Xue Li & Peiyuan Yu & Qiuling Song, 2022. "Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
    2. Nadim Eghbarieh & Nicole Hanania & Ahmad Masarwa, 2023. "Stereodefined polymetalloid alkenes synthesis via stereoselective boron-masking of polyborylated alkenes," Nature Communications, Nature, vol. 14(1), pages 1-11, December.

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