Prev. Article Next Article Table of Contents

Article

Guanidine/Pd(OAc)₂-Catalyzed Room Temperature Suzuki Cross-Coupling Reaction in Aqueous Media under Aerobic Conditions

Supporting Info

Shenghai Li,^† Yingjie Lin,^‡ Jungang Cao,^‡ and Suobo Zhang*^†

State Key Laboratory of Polymer and Chemistry, Changchun Institute of Applied Chemistry, Changchun 130022, China, and College of Chemistry, Jilin University, Changchun 130023, China

J. Org. Chem., 2007, 72 (11), pp 4067–4072

DOI: 10.1021/jo0626257

Publication Date (Web): April 28, 2007

†

Changchun Institute of Applied Chemistry.

‡

Jilin University.

Author to whom correspondence should be addressed. Fax: +86-431-85262117. Phone: +86-431-85262118.

, sbzhang@ciac.jl.cn

Abstract

A highly efficient Pd(OAc)₂/guanidine aqueous system for the room temperature Suzuki cross-coupling reaction has been developed. The new water-soluble and air-stable catalyst Pd(OAc)₂·(1f)₂ from Pd(OAc)₂ and 1,1,3,3-tetramethyl-2-n-butylguanidine (1f) was synthesized and characterized by X-ray crystallography. In the presence of Pd(OAc)₂·(1f)₂, coupling of arylboronic acids with a wide range of aryl halides, including aryl iodides, aryl bromides, even activated aryl chlorides, was carried out smoothly in aqueous solvent to afford the cross-coupling products in good to excellent yields and high turnover numbers (TONs) (TONs up to 850 000 for the reaction of 1-iodo-4-nitrobenzene and phenylboronic acid). Furthermore, this mild protocol could tolerate a broad range of functional groups.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue May 25, 2007
Received December 21, 2006

Recommend & Share

Related Content

Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki−Miyaura and Buchwald−Hartwig Reactions Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki−Miyaura and Buchwald−Hartwig ReactionsJournal of the American Chemical Society
- Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki−Miyaura and Buchwald−Hartwig Reactions Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki−Miyaura and Buchwald−Hartwig Reactions
  Nicolas Marion, Oscar Navarro, Jianguo Mei, Edwin D. Stevens, Natalie M. Scott, and Steven P. Nolan
  Journal of the American Chemical Society 2006 128 (12), pp 4101–4111
  Abstract: A series of (NHC)Pd(R-allyl)Cl complexes [NHC: IPr = N,N‘-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = N,N‘-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene; R = H, Me, gem-Me₂, Ph] have been synthesized and fully characterized. When ...
  Abstract | Full Text HTML | Hi-Res PDF
Phosphine-Free Palladium Acetate Catalyzed Suzuki Reaction in WaterThe Journal of Organic Chemistry
- Phosphine-Free Palladium Acetate Catalyzed Suzuki Reaction in Water
  Leifang Liu, Yuhong Zhang, and Yanguang Wang
  The Journal of Organic Chemistry 2005 70 (15), pp 6122–6125
  Abstract: Pd(OAc)₂ in a mixture of water and poly(ethylene glycol) (PEG) is shown to be an extremely active catalyst for the Suzuki reaction of aryl iodides and bromides. The reaction can be conducted under mild conditions (50 °C) without the use of a microwave or ...
  Abstract | Full Text HTML | Hi-Res PDF
Boronic Acids: New Coupling Partners in Room-Temperature Suzuki Reactions of Alkyl Bromides. Crystallographic Characterization of an Oxidative-Addition Adduct Generated under Remarkably Mild ConditionsJournal of the American Chemical Society
- Boronic Acids: New Coupling Partners in Room-Temperature Suzuki Reactions of Alkyl Bromides. Crystallographic Characterization of an Oxidative-Addition Adduct Generated under Remarkably Mild Conditions
  Jan H. Kirchhoff, Matthew R. Netherton, Ivory D. Hills, and Gregory C. Fu
  Journal of the American Chemical Society 2002 124 (46), pp 13662–13663
  Abstract: The Suzuki reaction is an exceptionally useful cross-coupling process that has been widely applied in synthetic chemistry, and boronic acids are, by far, the most commonly employed coupling partner. To date, however, no versatile method has been developed ...
  Abstract | Full Text HTML | Hi-Res PDF

Article

Guanidine/Pd(OAc)₂-Catalyzed Room Temperature Suzuki Cross-Coupling Reaction in Aqueous Media under Aerobic Conditions