Highly Active Catalyst for the Heterogeneous Suzuki−Miyaura Reaction:  Assembled Complex of Palladium and Non-Cross-Linked Amphiphilic Polymer

Yoichi M. A. Yamada, Koji Takeda, Hideyo Takahashi, and Shiro Ikegami*
Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa 199-0195, Japan
J. Org. Chem., 2003, 68 (20), pp 7733–7741
DOI: 10.1021/jo034354v
Publication Date (Web): September 9, 2003
Copyright © 2003 American Chemical Society

Abstract

Abstract Image

An assembled insoluble catalyst, PdAS, prepared from palladium ((NH4)2PdCl4 (1)) and non-cross-linked amphiphilic copolymer poly(N-isopropylacrylamide-co-4-diphenylstyrylphosphine) (2) was developed. It was found that PdAS is an excellent catalyst for the Suzuki−Miyaura reaction on three points:  (1) The use of 8 × 10-7 to 5 × 10-4 mol equiv of PdAS afforded the coupling products efficiently after easy workup, with the turnover number reaching up to 1 250 000. (2) The catalyst was reusable many times without loss of catalytic activity. (3) PdAS showed good stability in any reaction medium (i.e., water or aqueous or anhydrous organic solvents). Analytical study of PdAS indicates that the phosphines in 2 coordinate to palladium to form PdCl2(PPh2Ar)2 species.

Citing Articles

View all 59 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 22 ACS Journal articles (5 most recent appear below).

Tools

SciFinder Links

SciFinder subscribers:  Click to sign in | Not a SciFinder subscriber? Learn more at www.cas.org

Explore by:


History

  • Published In Issue October 03, 2003
  • Received March 18, 2003

Recommend & Share

  • Share on ACS NetworkACS Network
  • Add to FacebookFacebook
  • Tweet ThisTweet This
  • Add to CiteULikeCiteULike
  • Add to NewsvineNewsvine
  • Digg ThisDigg This
  • Add to DeliciousDelicious

Related Content

Other ACS content by these authors: