インジウム触媒を用いた直接的・効率的分子変換法の開発 [in Japanese] Direct and Efficient Organic Synthesis Using Indium Catalysts [in Japanese]
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An indium-catalyzed reductive Friedel-Crafts reaction using chlorohydrosilane with carbonyls in aromatic solvents gave alkylated aromatics. When allylsilane was used instead of aromatics, hydro-allylation of carbonyls proceeded in high yield. A direct substitution of OH group in alcohols was also catalyzed by indium compounds in the reaction with silyl nucleophiles. The system provides the direct reduction, chlorination, allylation, or alkynylation pathways for substitution of alcohols in a catalytic manner. The direct reaction of alcohols with active methylene compounds instead of silyl nucleophiles catalyzed by InCl<SUB>3</SUB> was accomplished without any activator or promoter. Allylic alcohols and benzylic alcohols served as electrophiles. α-Methoxyketone and indoles as nucleophiles were applicable to this system. Since H<SUB>2</SUB>O is the only side product of this system, the alkylated products were easily isolated in pure form. Indium compounds that have moderate (not strong) Lewis acidity and oxophilicity enables the catalytic reactions effectively.
- J. Synth. Org. Chem. Jpn.
J. Synth. Org. Chem. Jpn. 65(2), 99-108, 2007-02-01
The Society of Synthetic Organic Chemistry, Japan