A Novel Deprotonative Functionalization of Aromatics with Phosphazene Base

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Other Title
  • フォスファゼン塩基を用いる芳香環化合物の新規脱プロトン—修飾反応
  • フォスファゼン塩基を用いる芳香環化合物の新規脱プロトン--修飾反応
  • フォスファゼン エンキ オ モチイル ホウコウカン カゴウブツ ノ シンキ ダツプロトン シュウショク ハンノウ

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Description

  A novel type of deprotonative functionalization of aromatics was accomplished with a phosphazene base (t-Bu-P4 base). For various nitrogen heteroaromatics and benzene derivatives, deprotonative 1,2-additions proceeded with the t-Bu-P4 base and ZnI2 as an additive in the presence of carbonyl compounds. The t-Bu-P4 base has both extremely strong Brønsted basicity and less nucleophilicity due to its huge, widely conjugated structure, and highly chemoselective deprotonations were achieved. In addition the nonmetallic t-Bu-P4 base should not function as a Lewis acid. Therefore the deprotonation with the t-Bu-P4 base is considered to proceed via a different pathway from traditional deprotonative metalation of aromatics with metallic bases. Some reactions with unique regioselectivities were observed.<br>

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 124 (8), 509-517, 2004-08-01

    The Pharmaceutical Society of Japan

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