Direct Conversion of Carbonyl Compounds into Organic Halides:  Indium(III) Hydroxide-Catalyzed Deoxygenative Halogenation Using Chlorodimethylsilane

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Abstract

The reaction of carbonyls and chlorodimethylsilane was effectively catalyzed by indium(III) hydroxide and afforded the corresponding deoxygenative chlorination products, in which the carbonyl carbon accepted two nucleophiles (H and Cl) with releasing oxygen. Only In(OH)₃ catalyzed the reaction, and typical Lewis acids such as TiCl₄, AlCl₃, and BF₃·OEt₂ showed no catalytic activity. The reaction mechanism of this deoxygenative chlorination includes initial hydrosilylation followed by chlorination. Other nucleophiles such as allyl or iodine were available for this methodology. The moderate Lewis acidity of indium catalyst enabled chemoselective reaction, and therefore ester, nitro, cyano, or halogen groups were not affected during the reaction course.

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This article has been cited by 13 ACS Journal articles (5 most recent appear below).

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  Indium-Catalyzed Highly Efficient Three-Component Coupling of Aldehyde, Alkyne, and Amine via C−H Bond Activation

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  Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic Approach

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