Prev. Article Next Article Table of Contents

Note

Single and Double Suzuki−Miyaura Couplings with Symmetric Dihalobenzenes

Supporting Info

David J. Sinclair and Michael S. Sherburn*

Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia sherburn@rsc.anu.edu.au

J. Org. Chem., 2005, 70 (9), pp 3730–3733

DOI: 10.1021/jo050105q

Publication Date (Web): March 24, 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.

Abstract

m- or p-diiodobenzene undergoes selective double coupling reactions with arylboronic acids and esters. Selectivity for double coupling over single coupling is remarkably strong: even with a diiodobenzene:monoboronic acid ratio of 10:1, the products of double coupling are formed in good yields. Steric hindrance and electronic influences of the boronic acid or ester, and reaction conditions do not appear to impact significantly upon the outcome of the reaction. In contrast, m- and p-dibromobenzenes undergo single couplings with aryl boronic acids with high selectivity.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue April 29, 2005
Received January 18, 2005

Recommend & Share

Related Content

Preferential Oxidative Addition in Palladium(0)-Catalyzed Suzuki Cross-Coupling Reactions of Dihaloarenes with Arylboronic AcidsJournal of the American Chemical Society
- Preferential Oxidative Addition in Palladium(0)-Catalyzed Suzuki Cross-Coupling Reactions of Dihaloarenes with Arylboronic Acids
  Cheng-Guo Dong and Qiao-Sheng Hu
  Journal of the American Chemical Society 2005 127 (28), pp 10006–10007
  Abstract: The study of Pd(0)-/t-Bu₃P system as a powerful catalyst for the cross-coupling of n,m-dihaloarenes with 1 equiv of arylboronic acids is described. Our work demonstrated that the fate of the regenerated Pd(0) catalyst can be controlled when the ...
  Abstract | Full Text HTML | Hi-Res PDF
Preferential Oxidative Addition in Suzuki Cross-Coupling Reactions Across One Fluorene UnitOrganic Letters
- Preferential Oxidative Addition in Suzuki Cross-Coupling Reactions Across One Fluorene Unit
  Sven K. Weber, Frank Galbrecht, and Ullrich Scherf
  Organic Letters 2006 8 (18), pp 4039–4041
  Abstract: The Suzuki-type cross-coupling reaction of 2,7-dihalofluorenes with 1 equiv of arylboronic acid and Pd₂(dba)₃/P(t-Bu₃) as a catalyst system is investigated. The exclusive formation of the diarylated coupling product demonstrates that “preferential ...
  Abstract | Full Text HTML | Hi-Res PDF
Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild ConditionsJournal of the American Chemical Society
- Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions
  Adam F. Littke, Chaoyang Dai, and Gregory C. Fu
  Journal of the American Chemical Society 2000 122 (17), pp 4020–4028
  Abstract: Through the use of Pd₂(dba)₃/P(t-Bu)₃ as a catalyst, a wide range of aryl and vinyl halides, including chlorides, undergo Suzuki cross-coupling with arylboronic acids in very good yield, typically at room temperature; through use of Pd(OAc)₂/PCy₃, a ...
  Abstract | Full Text HTML | Hi-Res PDF

Note

Single and Double Suzuki−Miyaura Couplings with Symmetric Dihalobenzenes

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Preferential Oxidative Addition in Palladium(0)-Catalyzed Suzuki Cross-Coupling Reactions of Dihaloarenes with Arylboronic Acids

Preferential Oxidative Addition in Suzuki Cross-Coupling Reactions Across One Fluorene Unit

Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES