Copper-catalyzed Conjugate Addition of Organoboronic Acids and Esters to Electron-Deficient Alkynes

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  • 銅触媒を用いる有機ボロン酸類の電子欠損性アルキンへの共役付加反応
  • ドウ ショクバイ オ モチイル ユウキ ボロン サンルイ ノ デンシ ケッソンセイ アルキン エ ノ キョウヤク フカ ハンノウ

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In the presence of catalytic amounts of copper salts, CuOAc or Cu(OAc)2, the reaction of arylboronic acids with electron-deficient alkynes proceeded in MeOH at ambient temperature to afford hydroarylation products with high chemo- and stereoselectivity. This method of synthesizing tri-substituted alkenes was further applied to the synthesis of biologically interesting molecules such as butenolides/pentenolides, 4-arylcoumarins, 3,3-diarylacrylonitriles, and 3-arylindole-2-carboxylates. Among them, the tandem hydroarylation/lactonization leading to 4-arylcoumarins is particularly fascinating as seven natural products were synthesized by the combination of three alkynoates and four boronic acids.<br>The copper-catalyzed conjugate addition was further extended to that of allylboronates as organoboron reagents. Thus, the copper-catalyzed conjugate allylation of various electron-deficient alkynes was achieved and the derivatization of the introduced allyl moiety was also investigated.

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