Literature DB >> 22199404

Double Couplings of Dibromothiophenes using Boronic Acids and Boronates.

Samantha Varello1, Scott T Handy.   

Abstract

One-pot double couplings of dibromothiophenes have been investigated. Standard Suzuki couplings work well for 2,4-dibromothiophene, but are much more sensitive to steric effects in the case of 2,3-dibromothiophene. By using the recently reported potassium borates, though, good yields for both dibromothiophene isomers can be achieved.

Entities:  

Year:  2009        PMID: 22199404      PMCID: PMC3245682          DOI: 10.1002/chin.200919105

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN: 0039-7881            Impact factor:   3.157


  7 in total

Review 1.  Furans, thiophenes and related heterocycles in drug discovery.

Authors:  Jeffrey B Sperry; Dennis L Wright
Journal:  Curr Opin Drug Discov Devel       Date:  2005-11

2.  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

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

Authors:  Scott T Handy; Diyar Mayi
Journal:  Tetrahedron Lett       Date:  2007-11-12       Impact factor: 2.415

4.  Palladium-catalyzed selective 2,3-diarylation of alpha,alpha-disubstituted 3-thiophenemethanols via cleavage of C-H and C-C bonds.

Authors:  Masaya Nakano; Tetsuya Satoh; Masahiro Miura
Journal:  J Org Chem       Date:  2006-10-13       Impact factor: 4.354

5.  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

6.  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

7.  Cyclic triolborates: air- and water-stable ate complexes of organoboronic acids.

Authors:  Yasunori Yamamoto; Miho Takizawa; Xiao-Qiang Yu; Norio Miyaura
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

  7 in total

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