Synthetic Aryne Chemistry toward Multicomponent Coupling

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  • 多成分集積を指向した合成のためのアライン化学
  • タセイブン シュウセキ オ シコウ シタ ゴウセイ ノ タメ ノ アライン カガク

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Abstract

<p>Arynes with a highly reactive carbon-carbon triple bond are multipotent intermediates useful for preparing various multisubstituted arenes. To further enhance the synthetic utility of arynes, we have developed a wide range of synthetic methods involving aryne intermediates, including novel methods for aryne generation from o-sulfinylaryl triflates and o-iodoaryl triflates using phenyl or silylmethyl Grignard reagent, respectively. These methods allowed for the generation of new types of aryne intermediates that enabled facile syntheses of a wide variety of multisubstituted arenes such as aryl triflates, anilines, and benzoheterols. We also developed several novel transformations involving C-S or C-P bond formation via aryne intermediates, such as thioamination using sulfilimines, and several methods for preparing various o-silylaryl triflate-type aryne precursors that were difficult to be achieved by the conventional methods. These methods were demonstrated useful for preparation of a diverse range of multitriazoles and multisubstituted o-(arylthio)anilines by modular syntheses.</p>

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