Prev. Article Next Article Table of Contents

Note

InCl₃/I₂-Catalyzed Cross-Coupling of Alkyl Trimethylsilyl Ethers and Allylsilanes via an in Situ Derived Combined Lewis Acid of InCl₃ and Me₃SiI

Supporting Info

Takahiro Saito, Yoshihiro Nishimoto, Makoto Yasuda, and Akio Baba*

Department of Applied Chemistry, Center for Atomic and Molecular Technologies (CAMT), Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan baba@chem.eng.osaka-u.ac.jp

J. Org. Chem., 2007, 72 (22), pp 8588–8590

DOI: 10.1021/jo7015289

Publication Date (Web): October 3, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Direct C_sp3−C_sp3 coupling of various aliphatic trimethylsilyl ethers and allylsilanes is effectively catalyzed by InCl₃ and I₂. The transformation is thought to involve an in situ-derived combined Lewis acid of InCl₃ and Me₃SiI. The reaction can be used for the construction of quaternary−quaternary and quaternary−tertiary carbon−carbon bonds. This system enabled a highly chemoselective coupling to be conducted with a trimethylsilyl ether including an aryl halide moiety. Furthermore, couplings were possible using an alkynyltrimethylsilane and a trimethylsilyl ketene acetal.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue October 26, 2007
Received July 12, 2007

Recommend & Share

Related Content

Direct Coupling Reaction between Alcohols and Silyl Compounds: Enhancement of Lewis Acidity of Me₃SiBr Using InCl₃The Journal of Organic Chemistry
- Direct Coupling Reaction between Alcohols and Silyl Compounds: Enhancement of Lewis Acidity of Me₃SiBr Using InCl₃
  Takahiro Saito, Yoshihiro Nishimoto, Makoto Yasuda, and Akio Baba
  The Journal of Organic Chemistry 2006 71 (22), pp 8516–8522
  Abstract: The combination of InCl₃ and Me₃SiBr provided an enhanced Lewis acid system that can be used to promote a wide range of direct coupling reactions between alcohols and silyl nucleophiles in non-halogenated solvents, such as hexane or MeCN. The enhanced ...
  Abstract | Full Text HTML | Hi-Res PDF
Asymmetric [4 + 3] Cycloadditions between Vinylcarbenoids and Dienes: Application to the Total Synthesis of the Natural Product (−)-5-epi-Vibsanin EJournal of the American Chemical Society
- Asymmetric [4 + 3] Cycloadditions between Vinylcarbenoids and Dienes: Application to the Total Synthesis of the Natural Product (−)-5-epi-Vibsanin E
  Brett D. Schwartz, Justin R. Denton, Yajing Lian, Huw M. L. Davies and Craig M. Williams
  Journal of the American Chemical Society 2009 131 (23), pp 8329–8332
  Abstract: The total synthesis of (−)-5-epi-vibsanin E (2) has been achieved in 18 steps. The synthesis combines the rhodium-catalyzed [4 + 3] cycloaddition between a vinylcarbenoid and a diene to rapidly generate the tricyclic core with an effective end game ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Water Overcomes Methyl Group Directing Effects in Epoxide-Opening CascadesJournal of the American Chemical Society
- Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades
  Christopher J. Morten and Timothy F. Jamison
  Journal of the American Chemical Society 2009 131 (19), pp 6678–6679
  Abstract: Water is an effective promoter of the endo-selective opening of trisubstituted epoxides, enabling related cascades leading to a variety of substituted ladder polyether structures. When used in conjunction with a tetrahydropyran-templated nucleophile, ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Note

InCl₃/I₂-Catalyzed Cross-Coupling of Alkyl Trimethylsilyl Ethers and Allylsilanes via an in Situ Derived Combined Lewis Acid of InCl₃ and Me₃SiI