Prev. Article Next Article Table of Contents

Letter

Triethylsilane−Indium(III) Chloride System as a Radical Reagent

Supporting Info

Naoki Hayashi, Ikuya Shibata, and Akio Baba*

Department of Molecular Chemistry, Science and Technology Center for Atoms, Molecules and Ions Control (STAMIC), Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

Org. Lett., 2004, 6 (26), pp 4981–4983

DOI: 10.1021/ol047849v

Publication Date (Web): December 1, 2004

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

, baba@chem.eng.osaka-u.ac.jp

Abstract

A novel generation method of indium hydride (Cl₂InH) was found by the transmetalation of InCl₃ with Et₃SiH. In the intramolecular cyclization of enynes, the previously reported system (NaBH₄−InCl₃) has a problem of side reactions with the coexistent borane. In contrast, the problem was solved by the presented system, which affords effective hydroindation of alkynes.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue December 23, 2004
Received October 18, 2004

Recommend & Share

Related Content

Indium(III) Chloride−Sodium Borohydride System: A Convenient Radical Reagent for an Alternative to Tributyltin Hydride SystemJournal of the American Chemical Society
- Indium(III) Chloride−Sodium Borohydride System: A Convenient Radical Reagent for an Alternative to Tributyltin Hydride System
  Katsuyuki Inoue, Akemi Sawada, Ikuya Shibata, and Akio Baba
  Journal of the American Chemical Society 2002 124 (6), pp 906–907
  Abstract: The indium hydride generated from NaBH₄ and InCl₃, is a promising candidate of alternative to Bu₃SnH. In particular, the catalytic performance of InCl₃ in the dehalogenation of alkyl and aryl halides, intramolecular cyclization and intermolecular coupling ...
  Abstract | Full Text HTML | Hi-Res PDF
Stereoselective Synthesis of 3-Alkylideneoxindoles Using Tandem In-Mediated Carbometalation and Pd-Catalyzed Cross-Coupling ReactionOrganic Letters
- Stereoselective Synthesis of 3-Alkylideneoxindoles Using Tandem In-Mediated Carbometalation and Pd-Catalyzed Cross-Coupling Reaction
  Reiko Yanada, Shingo Obika, Munetaka Oyama, and Yoshiji Takemoto
  Organic Letters 2004 6 (16), pp 2825–2828
  Abstract: Efficient methods for stereoselective synthesis of various (E)-, (Z)-, and disubstituted 3-alkylideneoxindoles were investigated using tandem In-mediated carbometalation and ligandless Pd-catalyzed coupling reaction.
  Abstract | Full Text HTML | Hi-Res PDF
A Hierarchy of Aryloxide Deprotection by Boron TribromideOrganic Letters
- A Hierarchy of Aryloxide Deprotection by Boron Tribromide
  Sreenivas Punna, Stéphane Meunier, and M. G. Finn
  Organic Letters 2004 6 (16), pp 2777–2779
  Abstract: Aryl propargyl ethers and esters are cleaved selectively in the presence of aryl methyl ethers and esters by boron tribromide in dichloromethane. Under the same conditions, allyl ethers undergo very rapid Claisen rearrangement, and benzyl ethers are also ...
  Abstract | Full Text HTML | Hi-Res PDF

Letter

Triethylsilane−Indium(III) Chloride System as a Radical Reagent

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Indium(III) Chloride−Sodium Borohydride System: A Convenient Radical Reagent for an Alternative to Tributyltin Hydride System

Stereoselective Synthesis of 3-Alkylideneoxindoles Using Tandem In-Mediated Carbometalation and Pd-Catalyzed Cross-Coupling Reaction

A Hierarchy of Aryloxide Deprotection by Boron Tribromide

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES