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Coupling Reaction of Alkyl Chlorides with Silyl Enolates Catalyzed by Indium Trihalide
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Section:Abstract
Indium(III) halide catalyzed not only the coupling of alkyl chlorides with silyl enolates derived from esters, ketones, and aldehydes to give a variety of α-alkylated carbonyl compounds but also one-pot, three-component reactions of aldehyde enolate, alkyl chloride, and allylsilane or alkynylsilane.
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
Indium(III)-Catalyzed Asymmetric Hetero-Diels–Alder Reaction of Brassard-Type Diene with Aliphatic Aldehydes
Lili Lin, Yulong Kuang, Xiaohua Liu, and Xiaoming FengOrganic Letters2011 Article ASAPIndium(III)-Catalyzed Asymmetric Hetero-Diels–Alder Reaction of Brassard-Type Diene with Aliphatic Aldehydes
Lili Lin, Yulong Kuang, Xiaohua Liu, and Xiaoming FengOrganic Letters2011 Article ASAPA highly diastereo- and enantioselective hetero-Diels–Alder (HDA) reaction of a Brassard-type diene with aliphatic aldehydes has been developed. The chiral N,N′-dioxide L2/In(OTf)3 complex was efficient toward the obtention of the corresponding β-methoxy-...
Regioselective Carboindation of Simple Alkenes with Indium Tribromide and Ketene Silyl Acetals
Yoshihiro Nishimoto, Hiroki Ueda, Yoshihiro Inamoto, Makoto Yasuda and Akio BabaOrganic Letters2010 12 (15), 3390-3393Regioselective Carboindation of Simple Alkenes with Indium Tribromide and Ketene Silyl Acetals
Yoshihiro Nishimoto, Hiroki Ueda, Yoshihiro Inamoto, Makoto Yasuda and Akio BabaOrganic Letters2010 12 (15), 3390-3393The regioselective carboindation of simple alkenes with indium tribromide and ketene silyl acetals was accomplished. Various alkenes such as ethylene, 1-alkenes, and cyclic alkenes were applicable for this reaction system. The alkylindium product from ...
Iridium-Catalyzed α-Alkylation of Acetates with Primary Alcohols and Diols
Yosuke Iuchi, Yasushi Obora and Yasutaka IshiiJournal of the American Chemical Society2010 132 (8), 2536-2537Iridium-Catalyzed α-Alkylation of Acetates with Primary Alcohols and Diols
Yosuke Iuchi, Yasushi Obora and Yasutaka IshiiJournal of the American Chemical Society2010 132 (8), 2536-2537Acetates were successfully alkylated with primary alcohols and α,ω-diols in the presence of tert-BuOK under the influence of [IrCl(cod)]2. For instance, the reaction of tert-butyl acetate with n-butanol in the presence of tert-BuOK as a base and [IrCl(cod)...
An Expeditious Entry to Benzylic and Allylic Sulfones through Byproduct-Catalyzed Reaction of Alcohols with Sulfinyl Chlorides
Hai-Hua Li, De-Jun Dong, Yin-Huan Jin and Shi-Kai TianThe Journal of Organic Chemistry2009 74 (24), 9501-9504An Expeditious Entry to Benzylic and Allylic Sulfones through Byproduct-Catalyzed Reaction of Alcohols with Sulfinyl Chlorides
Hai-Hua Li, De-Jun Dong, Yin-Huan Jin and Shi-Kai TianThe Journal of Organic Chemistry2009 74 (24), 9501-9504In the absence of external catalysts and additives, a broad range of benzylic and allylic alcohols react with various sulfinyl chlorides to afford structurally diversified benzylic and allylic sulfones in moderate to excellent yields, and importantly, a ...
Radical Coupling of Iodocarbonyl Compounds with Butenylindium Generated by Transmetalation between Cyclopropylmethylstannane and Indium Halides
Makoto Yasuda, Kensuke Kiyokawa, Kenji Osaki and Akio BabaOrganometallics2009 28 (1), 132-139Radical Coupling of Iodocarbonyl Compounds with Butenylindium Generated by Transmetalation between Cyclopropylmethylstannane and Indium Halides
Makoto Yasuda, Kensuke Kiyokawa, Kenji Osaki and Akio BabaOrganometallics2009 28 (1), 132-139The reaction of cyclopropylmethylstannane with α-iodocarbonyl compounds in the presence of either InBr3 or InCl3 gave the C−C coupling products, cyclopropylethyl-substituted carbonyl compounds. Transmetalation between cyclopropylmethylstannane and indium ...
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History
- Published In Issue November 22, 2007
- Received July 26, 2007
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