Synthesis of tetraaryl-p-benzoquinones by Suzuki–Miyaura cross-coupling reactions of tetrabromo-p-benzoquinone

Ullah, Ihsan; Khera, Rasheed Ahmad; Hussain, Munawar; Villinger, Alexander; Langer, Peter

doi:10.1016/j.tetlet.2009.05.115

Cited by 22 publications

(11 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…201 The Suzuki-Miyura reaction of 164 with phenyl boronic acid in the presence of Pd(PPh 3 ) 4 Gan et al 202 developed a new, convergent and versatile synthetic strategy for efficient synthesis of 2,5-disubstituted-3,6-dimethoxy-1,4-benzoquinones (167) from readily available molecules (Scheme 41). By two sequential Suzuki couplings, aromatic components can be selectively introduced into the dihalogenated benzoquinone scaffolds (166).…”

Section: Synthesis Of Higher 14-benzoquinones Derivatives By the Reamentioning

confidence: 99%

See 1 more Smart Citation

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

169

View full text Add to dashboard Cite

As 1,4-benzoquinonas são encontradas em toda a natureza, podendo ser sintetizadas por diversas estratégias. Esta revisão apresenta os desenvolvimentos recentes das metodologias de síntese, das reações de ciclo adição, da química computacional e dos estudos de pulso radiolítico. Destaca ainda a sua significância química e biológica e de seus compostos derivados.1,4-Benzoquinones are ubiquitous in nature and can be synthesized by diverse strategies. Recent developments on their synthetic methodologies, cycloaddition reactions, computational chemistry and pulse radiolytic studies are reported in this review. Their chemical and biological significance as well as their derivates' are also covered.

show abstract

Section: Synthesis Of Higher 14-benzoquinones Derivatives By the Reamentioning

confidence: 99%

“…Many well known quinones such as p-chloranil (200), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) (201) and tetracyano-p-benzoquinone (202) …”

Section: Computational Investigations On 14-benzoquinonesmentioning

confidence: 99%

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

169

View full text Add to dashboard Cite

show abstract

“…Scheme shows the synthetic procedure for 1 a and 1 b . Diiodo precursor monomers 2 a and 2 b , the key intermediates toward CHPBs, were prepared from 2,3,5,6‐tetraphenyl‐1,4‐benzoquinone8 in two steps (see the Supporting Information). Macrocyclization of 2 a and 2 b was achieved by Yamamoto coupling reactions 7h.…”

Section: Methodsmentioning

confidence: 99%

Three‐Dimensionally Arranged Cyclic p‐Hexaphenylbenzene: Toward a Bottom‐Up Synthesis of Size‐Defined Carbon Nanotubes

Nishiuchi

Feng

Enkelmann

et al. 2012

Chemistry A European J

115

View full text Add to dashboard Cite

show abstract

“…9 We have also reported the synthesis of tetraaryl-p-benzoquinones by Suzuki reactions of tetrabromo-p-benzoquinone. 10 Recently, we have reported that Suzuki-Miyaura reactions of the bis(triflate) of methyl 2,5-dihydroxybenzoate proceed with very good site selectivity in favor of the sterically less hindered position 5. 11 Herein, we report, for the first time, the synthesis of 1,2-diarylanthraquinones by Suzuki-Miyaura reactions of the bis(triflate) of 1,2-dihydroxyanthraquinone.…”

mentioning

confidence: 99%