Site-selective Suzuki–Miyaura cross-coupling reactions of 2,3,4,5-tetrabromofuran

Hussain, Munawar; Khera, Rasheed Ahmad; Hung, Nguyen Thai; Langer, Peter

doi:10.1039/c0ob00695e

Cited by 32 publications

(17 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Considering the lower aromaticity of furan compared to thiophene, we then switched to Pd(PPh 3 ) 4 as Pd(0) catalyst. 49 The dibromofurans were coupled with 5 equivalents of the aryl boronic acid and then deprotected with boron tribromide to give the final products 16a–d and 18a–d in moderate to good yields.…”

Section: Resultsmentioning

confidence: 99%

Thiophene-Core Estrogen Receptor Ligands Having Superagonist Activity

et al. 2013

View full text Add to dashboard Cite

To probe the importance of the heterocyclic core of estrogen receptor (ER) ligands, we prepared a series of thiophene-core ligands by Suzuki cross-coupling of aryl boronic acids with bromo-thiophenes, and we assessed their receptor binding and cell biological activities. The disposition of the phenol substituents on the thiophene core, at alternate or adjacent sites, and the nature of substituents on these phenols all contribute to binding affinity and subtype selectivity. Most of the bis(hydroxyphenyl)-thiophenes were ERβ selective, whereas the tris(hydroxyphenyl)-thiophenes were ERα selective; analogous furan-core compounds generally have lower affinity and less selectivity. Some diarylthiophenes show distinct superagonist activity in reporter gene assays, giving maximal activities 2–3 times that of estradiol, and modeling suggests that these ligands have a different interaction with a hydrogen-bonding residue in helix-11. Ligand-core modification may be a new strategy for developing ER ligands whose selectivity is based on having transcriptional activity greater than that of estradiol.

show abstract

Section: Resultsmentioning

confidence: 99%

Thiophene-Core Estrogen Receptor Ligands Having Superagonist Activity

et al. 2013

View full text Add to dashboard Cite

show abstract

“…The site‐selectivity is controlled by electronic and steric parameters . Recently, we have reported the synthesis of aryl‐substituted thiophenes , pyrroles , selenophenes , pyrimidines , and furans based on site‐selective Suzuki reactions of polyhalogenated heterocycles. In recent years, site‐selective Sonogashira , Negishi , and Stille coupling reactions of 2,3‐dibromobenzofuran and 2,6‐dibromobenzofuran have been studied.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Arylated Benzofurans by RegioselectiveSuzuki–Miyaura Cross‐Coupling Reactions of 2,3‐Dibromobenzofurans‐ and 2,3,5‐Tribromobenzofurans

Hussain

Hung

Abbas

et al. 2014

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…Highly site‐selective Suzuki–Miyaura cross‐coupling reactions of 2,3,4,5‐tetrabromofuran with arylboronic acids that allow the synthesis of 2‐aryl‐ and 2,5‐diarylfurans in high yields have been described 202…”

Section: Discussionmentioning

confidence: 99%

Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes

2012

View full text Add to dashboard Cite

The palladium-catalyzed Suzuki-Miyaura reaction of multiply halogenated, electron-rich and electron-deficient heteroarenes is one of the most reliable and environmentally friendly tools for installing a wide range of non-functionalized and functionalized carbon substituents onto heteroaromatic systems with exquisite chemo-and site-selectivity. For substrates with different halogen groups the chemoselectivity of the Suzuki-Miyaura reactions has been found to be dependent on the reactivity difference between the halogens. However, the hardest achievement of selectivity in Suzuki-Miyaura monocouplings involving polyhalogenated heteroarenes with identical halogen atoms has been shown to be dominated by steric and electronic effects and the presence of directing groups at positions neighbouring the reaction sites. Moreover, in the case of symmetrically substituted dihaloheteroarenes with identical halogen atoms, highly selective monocoupling reactions have often been achieved only after a careful optimization of reaction parameters including the catalyst precursor, base, solvent, and the molar ratio between electrophile and organoboron reagent. This critical review with 341 references covers developments on the chemo-and site-selective Suzuki-Miyaura monocoupling reactions of polyhalogenated heteroarenes with different or identical halogen atoms. It also includes the synthesis of polysubstituted heteroarenes, not easily accessible by other means, via consecutive monocoupling reactions and/ or a more synthetically valuable approach involving one-pot polycoupling reactions.

show abstract

Site-selective Suzuki–Miyaura cross-coupling reactions of 2,3,4,5-tetrabromofuran

Abstract: Suzuki-Miyaura reactions of 2,3,4,5-tetrabromofuran allow a convenient and site-selective synthesis of mono-, di- and tetraarylfurans which are not readily available by other methods.

Cited by 32 publications

References 42 publications

Thiophene-Core Estrogen Receptor Ligands Having Superagonist Activity

Thiophene-Core Estrogen Receptor Ligands Having Superagonist Activity

Synthesis of Arylated Benzofurans by RegioselectiveSuzuki–Miyaura Cross‐Coupling Reactions of 2,3‐Dibromobenzofurans‐ and 2,3,5‐Tribromobenzofurans

Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes

Contact Info

Product

Resources

About