3価のインジウム塩による活性化を基盤とした新しい有機合成反応の開発

概要

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Indium (III) salt has attracted considerable attention in synthetic organic chemistry due to its low toxicity, high stability under aqueous conditions, and strong tolerance to oxygen- and nitrogen containing functional groups. Hence, our interest focused on developing a novel synthetic organic reaction based on activation by the trivalent indium halide. Herein we report the following reactions: (i) an InBr3-Et3N reagent system-promoted alkynylation of aldehydes or N,O-acetals leading to various propargylic alcohols or amines; (ii) a Pd(II)-InBr3 reagent system-catalyzed cross-coupling reaction of terminal alkynes with aryl iodides leading to the functionalized alkyne derivatives; (iii) InBr3-catalyzed intramolecular cyclization of various ethynylanilines producing a variety of indole derivatives; (iv) InBr3-promoted intermolecular dimerization of the ethynylanilines without a substituent on a terminal alkyne affording polysubstituted quinolines; (v) an InBr3-Et3SiH reagent system-promoted chemoselective deoxygenation of esters, amides or nitrobenzenes producing the corresponding highly valuable compounds.