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Literature DB >> 19008934

Regioselective double Suzuki couplings of 4,5-dibromothiophene-2-carboxaldehyde.

Abstract

Conditions have been identified that enable the one-pot double Suzuki coupling of 4,5-dibromothiophene-2-carboxaldehyde to proceed in good yield. The key to success in these reactions is the use of minimal amounts of water to avoid significant amounts of dehalogenation during the first coupling.

Entities: Chemical

Year: 2007 PMID： 19008934 PMCID： PMC2128684 DOI： 10.1016/j.tetlet.2007.09.114

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

5 in total

1. A simple guide for predicting regioselectivity in the coupling of polyhaloheteroaromatics.

Authors: Scott T Handy; Yanan Zhang
Journal: Chem Commun (Camb) Date: 2005-11-21 Impact factor: 6.222

2. Air-stable trialkylphosphonium salts: simple, practical, and versatile replacements for air-sensitive trialkylphosphines. Applications in stoichiometric and catalytic processes.

Authors: M R Netherton; G C Fu
Journal: Org Lett Date: 2001-12-27 Impact factor: 6.005

3. Regioselective dicouplings: application to differentially substituted pyrroles.

Authors: Scott T Handy; Jesse J Sabatini
Journal: Org Lett Date: 2006-04-13 Impact factor: 6.005

4. Disubstituted pyridines: the double-coupling approach.

Authors: Scott T Handy; Thomas Wilson; Aaron Muth
Journal: J Org Chem Date: 2007-10-05 Impact factor: 4.354

5. Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions.

Authors: Diego A Alonso; Carmen Nájera; Ma Carmen Pacheco
Journal: J Org Chem Date: 2002-08-09 Impact factor: 4.354

5 in total

4 in total

Regioselective double Suzuki couplings of 4,5-dibromothiophene-2-carboxaldehyde.

1. A simple guide for predicting regioselectivity in the coupling of polyhaloheteroaromatics.

2. Air-stable trialkylphosphonium salts: simple, practical, and versatile replacements for air-sensitive trialkylphosphines. Applications in stoichiometric and catalytic processes.

3. Regioselective dicouplings: application to differentially substituted pyrroles.

4. Disubstituted pyridines: the double-coupling approach.

5. Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions.

1. Studies of one-pot double couplings on dibromoquinolines.

2. One-pot Double Suzuki Couplings of Dichloropyrimidines.

3. Pd/P(t-Bu)(3)-Catalyzed Suzuki Cross-Couplings in the Presence of Water.

4. Double Couplings of Dibromothiophenes using Boronic Acids and Boronates.