Chemistry of Chelate-Type Hypervalent Boron and Aluminum: Utilization for Selective Organic Synthesis.

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  • Uraguchi Daisuke
    Department of Chemistry, Graduate School of Science, Hokkaido University
  • Ooi Takashi
    Department of Chemistry, Graduate School of Science, Hokkaido University
  • Maruoka Keiji
    Department of Chemistry, Graduate School of Science, Hokkaido University

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Other Title
  • キレート型高配位ホウ素，アルミニウムの化学　　選択的有機合成への活用
  • キレートガタ コウハイイ ホウソ アルミニウム ノ カガク センタクテキ ユウキ ゴウセイ エ ノ カツヨウ
  • <I>Utilization for Selective Organic Synthesis</I>
  • 選択的有機合成への活用

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Abstract

In this review, the hypercoordination of boron and aluminum as typical main group elements is embodied, and their synthetic utility is demonstrated with several synthetic examples. B and Al Lewis acids are found to be successfully utilized in several chelation-controlled reactions of various substrates (alkoxy carbonyl compounds, fluoro carbonyl compounds, fluoro epoxides, and alkoxy epoxides) via unprecedented pentacoordinate chelate-type complex formation by taking advantage of the exceedingly high affinity of B and Al to fluorine and oxygen, and hence, contrary to the previous observations, can be classified as chelating Lewis acid reagents rather than non-chelating Lewis acids. In addition to the experimental demonstration, such pentacoordinate complex formation of B and Al Lewis acids with various bidentate substrates is also characterized by low-temperature 1H, 13c, 11B, 27AlNMR spectroscopy.

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