Prev. Article Next Article Table of Contents

Article

Synthesis of Functionalized Benzylsilanes from Arylzinc Compounds and (Iodomethyl)trimethylsilane by Means of a Novel Rh Catalysis

Supporting Info

Hideki Takahashi, Kabir M. Hossain, Yasushi Nishihara, Takanori Shibata, and Kentaro Takagi*

Department of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700-8530, Japan

J. Org. Chem., 2006, 71 (2), pp 671–675

DOI: 10.1021/jo0520994

Publication Date (Web): December 14, 2005

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

, takagi@cc.okayama-u.ac.jp

Abstract

The catalytic activity of a Rh complex in cross-coupling between ArZnI and TMSCH₂I was examined in which the Rh complex, generated in situ from [RhCl(1,5-cyclooctadiene)]₂ and 1,1‘-bis(diphenylphosphino)ferrocene, exhibited excellent catalytic activity for the production of various functionalized benzylsilanes in good yields. From ³¹P NMR studies of various solutions containing several of the reaction components, confirmation of the rapid and quantitative transfer of aryl groups from ArZnI to the Rh complex to form arylrhodium species was ascertained. A catalytic cycle, commencing with the transmetalation, was thus proposed for the reaction.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue January 20, 2006
Received October 7, 2005

Recommend & Share

Related Content

Rh-Catalyzed Negishi Alkyl-Aryl Cross-Coupling Leading to α- or β-Phosphoryl-Substituted AlkylarenesThe Journal of Organic Chemistry
- Rh-Catalyzed Negishi Alkyl-Aryl Cross-Coupling Leading to α- or β-Phosphoryl-Substituted Alkylarenes
  Hideki Takahashi, Shinya Inagaki, Naoko Yoshii, Fuxing Gao, Yasushi Nishihara and Kentaro Takagi
  The Journal of Organic Chemistry 2009 74 (7), pp 2794–2797
  Abstract: The catalytic cross-coupling between ArZnX and ICH₂(CH₂)_nP(O)(OEt)₂ (n = 0−3) has been investigated to determine the utility of the Rh catalyst during the alkyl-aryl cross-coupling and to develop a new synthetic method for phosphoryl-substituted ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Novel Rh Catalysis in Cross-Coupling between Alkyl Halides and Arylzinc Compounds Possessing ortho-COX (X = OR, NMe₂, or Ph) GroupsOrganic Letters
- Novel Rh Catalysis in Cross-Coupling between Alkyl Halides and Arylzinc Compounds Possessing ortho-COX (X = OR, NMe₂, or Ph) Groups
  Hideki Takahashi, Shinya Inagaki, Yasushi Nishihara, Takanori Shibata, and Kentaro Takagi
  Organic Letters 2006 8 (14), pp 3037–3040
  Abstract: Rh−dppf was found to be an efficient catalyst for the cross-coupling between primary alkyl halides bearing β-hydrogens and arylzinc compounds possessing carbonyl groups such as ester, amide, or ketone at the ortho position. Various functional groups such ...
  Abstract | Full Text HTML | Hi-Res PDF
Synthesis of Aromatic Esters via Pd-Catalyzed Decarboxylative Coupling of Potassium Oxalate Monoesters with Aryl Bromides and ChloridesJournal of the American Chemical Society
- Synthesis of Aromatic Esters via Pd-Catalyzed Decarboxylative Coupling of Potassium Oxalate Monoesters with Aryl Bromides and Chlorides
  Rui Shang, Yao Fu, Jia-Bin Li, Song-Lin Zhang, Qing-Xiang Guo and Lei Liu
  Journal of the American Chemical Society 2009 131 (16), pp 5738–5739
  Abstract: Pd-catalyzed decarboxylative cross-coupling of aryl iodides, bromides, and chlorides with potassium oxalate monoesters has been discovered. This reaction is potentially useful for laboratory-scale synthesis of aryl and alkenyl esters. Bulky, electron-rich ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Article

Synthesis of Functionalized Benzylsilanes from Arylzinc Compounds and (Iodomethyl)trimethylsilane by Means of a Novel Rh Catalysis