イソニトリル金属錯体と有機合成化学への応用

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  • Application of Isonitrile-Metal Complexes to Organic Synthesis
  • イソニトリル キンゾク サクタイ ト ユウキ ゴウセイ カガク エ ノ オウヨウ

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This account outlines our studies on isonitrile-metal complexes and their application to organic synthesis.<br>Isonitriles possess an electronic structure which is similar to that of carbon monoxide. The carbene character brings about versatile reactivities as the reagent and interesting properties as the ligand. The α-hydorogen is highly acidic, and hence, the α-position is endowed with a nucleophilic character. Reduction of an alkylisonitrile with tin hydride affords alkane via a radical mechanism. Various organometallic reagents undergo α-addition to isonitriles and the resulting imidoylmetal intermediate acts as the acyl anion equivalent. Insertion of isonitriles into an Si-Si bond is catalyzed by palladium. A highly enantioselective aldol reaction of α-isocyanoesters with aldehydes is achieved by a gold catalyst. Isonitrile-Pd(0) complexes efficiently activate Si-Si and Si-B linkages, and unsaturated functionalities are inserted therein. Aromatizing polymerization of 1,2-diisocyanoarenes produces poly(quinoxaline)s which possess chiral helical structures. Enantiomerically enriched ones are successfully synthesized by using a chiral catalyst or auxiliary.

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