Prev. Article Next Article Table of Contents

Article

P(i-BuNCH₂CH₂)₃N: An Effective Ligand in the Palladium-Catalyzed Amination of Aryl Bromides and Iodides

Sameer Urgaonkar, M. Nagarajan, and J. G. Verkade*

Department of Chemistry, Gilman Hall, Iowa State University, Ames, Iowa 50011

J. Org. Chem., 2003, 68 (2), pp 452–459

DOI: 10.1021/jo0205309

Publication Date (Web): December 24, 2002

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

, jverkade@iastate.edu

Abstract

It is shown that the bicyclic triaminophosphine P(i-BuNCH₂CH₂)₃N serves as an effective ligand for the palladium-catalyzed amination of a wide array of aryl bromides and iodides. Other bicyclic or acyclic triaminophosphines, even those of similar basicity and/or bulk, were inferior.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue January 24, 2003
Received August 9, 2002

Recommend & Share

Related Content

A Second-Generation Catalyst for Aryl Halide Amination: Mixed Secondary Amines from Aryl Halides and Primary Amines Catalyzed by (DPPF)PdCl₂Journal of the American Chemical Society
- A Second-Generation Catalyst for Aryl Halide Amination: Mixed Secondary Amines from Aryl Halides and Primary Amines Catalyzed by (DPPF)PdCl₂
  Michael S. Driver and John F. Hartwig
  Journal of the American Chemical Society 1996 118 (30), pp 7217–7218
  Abstract | Full Text HTML | Hi-Res PDF
Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and TriflatesThe Journal of Organic Chemistry
- Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates
  John P. Wolfe, Hiroshi Tomori, Joseph P. Sadighi, Jingjun Yin, and Stephen L. Buchwald
  The Journal of Organic Chemistry 2000 65 (4), pp 1158–1174
  Abstract: Palladium complexes supported by (o-biphenyl)P(t-Bu)₂ (3) or (o-biphenyl)PCy₂ (4) are efficient catalysts for the catalytic amination of a wide variety of aryl halides and triflates. Use of ligand 3 allows for the room-temperature catalytic amination of ...
  Abstract | Full Text HTML | Hi-Res PDF
P[N(i-Bu)CH₂CH₂]₃N: A Versatile Ligand for the Pd-Catalyzed Amination of Aryl ChloridesOrganic Letters
- P[N(i-Bu)CH₂CH₂]₃N: A Versatile Ligand for the Pd-Catalyzed Amination of Aryl Chlorides
  Sameer Urgaonkar, M. Nagarajan, and John G. Verkade
  Organic Letters 2003 5 (6), pp 815–818
  Abstract: Palladium-catalyzed amination reactions of aryl chlorides with amines proceeded in the presence of the bicyclic triaminophosphine P[N(i-Bu)CH₂CH₂]₃N to afford the corresponding arylamines in good to excellent yields. Electron-poor, electron-neutral, and ...
  Abstract | Full Text HTML | Hi-Res PDF

Article

P(i-BuNCH₂CH₂)₃N: An Effective Ligand in the Palladium-Catalyzed Amination of Aryl Bromides and Iodides