Highly stereoselective synthesis of para-substituted (E)-N-styrylcarbazoles via sequential silylative coupling–Hiyama coupling reaction

Prukała, Wiesław; Marciniec, Bogdan; Majchrzak, Mariusz; Kubicki, Maciej

doi:10.1016/j.tet.2006.11.065

Cited by 19 publications

(24 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…oxy-(45.3 [11]), and slightly smaller than in halogeno-(53.6 -58.3 , [8]) derivatives. Only in nitro-substituted compounds these angles are significantly smaller (i.e.…”

Section: Molecular Geometrymentioning

confidence: 79%

See 1 more Smart Citation

Two polymorphs of 9-[(E)-2-(4-methylphenyl)ethenyl]-9H-carbazole, both with Z′ = 4

Kubicki¹,

Prukała

Marciniec

2009

Zeitschrift Für Kristallographie

Self Cite

View full text Add to dashboard Cite

Polymorphism / Carbazole derivatives / Weak intermolecular interactions / Crystal structure analysis / X-ray diffraction Abstract. The crystal structures of two polymorphic forms of 9-[(E)-2-(4-methylphenyl)ethenyl]-9H-carbazole have been determined. One of the structures is monoclinic: (2) , and the other is triclinic: (3) , and in both forms there are four symmetry-independent molecules in the asymmetric unit. The geometric parameters defining these molecules are similar with the normal probability plots showing that the differences between molecules are of a statistical rather than a systematic nature. In both structures there is a high degree of pseudo-symmetry between the symmetrically independent molecules. The crystal packing modes of both polymorphs are quite similar, the differences are found at the level of the composition of structural building blocks: stacks, layers and bi-layers.

show abstract

“…oxy-(45.3 [11]), and slightly smaller than in halogeno-(53.6 -58.3 , [8]) derivatives. Only in nitro-substituted compounds these angles are significantly smaller (i.e.…”

Section: Molecular Geometrymentioning

confidence: 79%

“…The synthesis of 9-[(E)-2-(4-methylphenyl)ethenyl]-9H-carbazole has been described elsewhere [11]. Crystals appropriate for X-ray diffraction experiments were obtained by slow evaporation from methanol solutions.…”

Section: Methodsmentioning

confidence: 99%

Two polymorphs of 9-[(E)-2-(4-methylphenyl)ethenyl]-9H-carbazole, both with Z′ = 4

Kubicki¹,

Prukała

Marciniec

2009

Zeitschrift Für Kristallographie

Self Cite

View full text Add to dashboard Cite

show abstract

“…The sequential silylative coupling-Hiyama coupling strategy has been successfully used for stereoselective synthesis of (E)-stilbenes, 45 (E)-9-styrylcarbazoles, 46 bis[(E)-styryl]arenes, 47 stilbenoid dendrimers 48 and arylene-(E)-vinylene polymers. The sequential silylative coupling-Hiyama coupling strategy has been successfully used for stereoselective synthesis of (E)-stilbenes, 45 (E)-9-styrylcarbazoles, 46 bis[(E)-styryl]arenes, 47 stilbenoid dendrimers 48 and arylene-(E)-vinylene polymers.…”

Section: Synthesis Of Aryl-vinyl Derivativesmentioning

confidence: 99%

Silylative coupling of olefins with vinylsilanes in the synthesis of functionalized alkenes

2015

View full text Add to dashboard Cite

The development of highly selective methods for the synthesis of functionalized olefins, based on sequential catalytic reactions of organometallic reagents, has been the subject of extensive study because of their versatile applications in organic synthesis and materials science. The silylative coupling of olefins with vinyl-substituted organosilicon compounds (discovered in our group) represents one of the most efficient and straightforward methods for the synthesis of stereodefined alkenylsilanes and bis (silyl) alkenes, which are particularly attractive scaffolds for further transformations including palladium-catalyzed cross-coupling with organic halides (Hiyama coupling) or electrophile-induced desilylation. The article highlights the recent developments and covers the literature mainly from the last decade in the sequential (also one-pot) synthetic strategies including ruthenium-catalyzed silylative coupling followed by desilylative cross-coupling, acylation and halogenation, leading to stereodefined organic derivatives such as (E)-alkenyl halides, (E)-α,β-unsaturated ketones or arylene-(E)-vinylene derivatives which are widely applied as fine chemicals, functional materials or building blocks in organic synthesis. † Dedicated to Prof. Ei-ichi Negishi on the occasion of his 80th birthday.

show abstract

“…In view of the above advantages, we have successfully applied various unsaturated organosilicon precursors such as ( E )-silylstyrenes [26,27,28], 1,1-bis(silyl)alkenes [29,30], ( E )-1,2-bis(silyl)alkenes [31] and vinylcyclosiloxanes [32] as versatile double-bond equivalents in the construction of π-conjugated systems.…”

Section: Introductionmentioning

confidence: 99%

1-(Triethoxysilyl)buta-1,3-dienes—New Building Blocks for Stereoselective Synthesis of Unsymmetrical (E,E)-1,4-Disubstituted 1,3-dienes

2015

View full text Add to dashboard Cite

show abstract

Highly stereoselective synthesis of para-substituted (E)-N-styrylcarbazoles via sequential silylative coupling–Hiyama coupling reaction

Cited by 19 publications

References 51 publications

Two polymorphs of 9-[(E)-2-(4-methylphenyl)ethenyl]-9H-carbazole, both with Z′ = 4

Two polymorphs of 9-[(E)-2-(4-methylphenyl)ethenyl]-9H-carbazole, both with Z′ = 4

Silylative coupling of olefins with vinylsilanes in the synthesis of functionalized alkenes

1-(Triethoxysilyl)buta-1,3-dienes—New Building Blocks for Stereoselective Synthesis of Unsymmetrical (E,E)-1,4-Disubstituted 1,3-dienes

Contact Info

Product

Resources

About