Vinyl- and Arylsilicon, germanium, and boron Compounds

Marciniec, Bogdan; Pietraszuk, Cezary; Kownacki, Ireneusz; Zaidlewicz, M.

doi:10.1016/b0-08-044655-8/00040-4

Cited by 20 publications

(18 citation statements)

References 519 publications

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“…(E)- 1-phenyl-2-(tri-n-butylgermyl) (6). Elemental analysis calcd (%) for C 26 H 37 GeN: C 71.59,H 8.55,N 3.21;found: C 71.52,H 8.51,N 3.19.…”

Section: Ge-ch Ch-r]mentioning

confidence: 99%

“…[5] While in the last two decades two new reactions of silicon derivatives catalyzed by TM metal complexes have been developed to provide universal routes for synthesis of organosilicon compounds of vinylsilicon functionality, i.e. silylation of olefins with hydrosilanes (dehydrogenative silylation) and silylation with vinylsilanes (silylative coupling) [for review see reference [6] ], only two reports on respective reactions of olefin germylation with hydrogermanes [7] and vinylgermanes [8] have recently appeared. By analogy to the respective silylation reactions, these two processes proceed in the presence of catalytic species containing initially or generating in situ M-H and M-Ge bonds (where M = Ru, Rh) via cleavage of the C-H bond of olefins and C-Ge and H-Ge of germanes.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of substituted vinylgermanes and germylsilylethenes via ruthenium complex catalyzed germylation of olefins

Marciniec

Ławicka

2008

Applied Organom Chemis

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A series of substituted vinylgermanes and divinylgermanes have been synthesized in moderate or high yield via two reactions of olefins and dienes catalyzed by [RuHCl(CO) (PCy 3 ) 2 ], i.e. germylative coupling with vinylgermanes and dehydrogenative germylation with hydrogermanes. While the former reaction can be a versatile way of regioselective synthesis of products (particularly useful for the stereoselective synthesis of germylsilylethenes), the latter could be used as a complement, especially in synthesis of germylate dioxol ethene and vinyl ethers.

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“…(E)- 1-phenyl-2-(tri-n-butylgermyl) (6). Elemental analysis calcd (%) for C 26 H 37 GeN: C 71.59,H 8.55,N 3.21;found: C 71.52,H 8.51,N 3.19.…”

Section: Ge-ch Ch-r]mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of substituted vinylgermanes and germylsilylethenes via ruthenium complex catalyzed germylation of olefins

Marciniec

Ławicka

2008

Applied Organom Chemis

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“…Indeed, a number of them have found clinical utility as drugs and antibacterial and antifungal compounds. [6][7] Boryl-substituted 1,3-dienes can be prepared by classic stoichiometric routes using organometallic reagents [10,11] or by more recently applied catalytic methods, such as hydroboration of enynes, [12] cross-coupling of 1,1-diborylated alkenes with alkenyl halides, [13] Heck coupling of vinylboronate with vinylarylic iodides, [8e, 14] as well as cross-metathesis of vinylboronates with 1,3-dienes. [15] Additionally, silylboryl-substituted dienes can be synthesised by means of nickel-catalysed silaborative dimerisation of alkynes.…”

Section: Introductionmentioning

confidence: 99%

A New Catalytic Route to Boryl‐ and Borylsilyl‐Substituted Buta‐1,3‐dienes

Walkowiak

Jankowska‐Wajda

Marciniec

2008

Chemistry A European J

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Vinyl-substituted boronates in the presence of complexes containing Ru-H bonds (preferably [Ru(CO)ClH(PCy(3))(2)], Cy: cyclohexyl) react regioselectively with terminal ethynes (involving silylethynes), albeit with the exception of phenylacetylene, to produce boryl- and borylsilyl-substituted buta-1,3-dienes with a preference for E,E-diene. The reaction opens a new catalytic route for the preparation of dienylboronates, and particularly dienylsilylboronates, that are functionalised building blocks in the synthesis of organic and natural products. The mechanism of this new reaction was proved to involve an insertion of alkyne into Ru-H bonds followed by an insertion of coordinated vinyl boronate into the Ru-C= bond and beta-hydrogen transfer to the metal to eliminate boryldiene or borylsilyldiene.

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“…Many efficient stereo‐ and regioselective methodologies for the synthesis of vinylsilanes involve classical stoichiometric routes from organometallic reagents or, recently, TM‐catalysed transformations of alkynes, silylalkynes, alkenes and – in particular – terminal vinylsilanes 2…”

Section: Introductionmentioning

confidence: 99%

Silylative Coupling of Olefins with Vinylsilanes in the Synthesis of π‐Conjugated Double Bond Systems

2009

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The design and development of highly efficient and selective methods for the synthesis of π‐conjugated arylvinyl derivatives, based on sequential catalytic reactions of organometallic reagents, have been the subject of extensive study because of their versatile application in organic synthesis and materials science. The silylative coupling of olefins with vinyl‐substituted silicon compounds represents one of the most efficient and selective methods for the synthesis of alkenylsilanes, which are particularly attractive scaffolds for further transformations, including transition‐metal‐catalysed cross‐coupling with organic halides or substitution with organic and inorganic electrophiles. The microreview highlights recent developments in sequential synthetic strategies including ruthenium‐catalysed silylative coupling followed by desilylative cross‐coupling and halogenation, leading to stereodefined organic derivatives containing arylene‐vinylene units widely applied as fine chemicals, functional materials or unsaturated building blocks in organic synthesis.

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Vinyl- and Arylsilicon, germanium, and boron Compounds

Cited by 20 publications

References 519 publications

Synthesis of substituted vinylgermanes and germylsilylethenes via ruthenium complex catalyzed germylation of olefins

Synthesis of substituted vinylgermanes and germylsilylethenes via ruthenium complex catalyzed germylation of olefins

A New Catalytic Route to Boryl‐ and Borylsilyl‐Substituted Buta‐1,3‐dienes

Silylative Coupling of Olefins with Vinylsilanes in the Synthesis of π‐Conjugated Double Bond Systems

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