Synthesis of functionalized styrenes via palladium-catalyzed coupling of aryl bromides with vinyl tin reagents

McKean, Dennis R.; Parrinello, G.; Renaldo, A. F.; Stille, J. K.

doi:10.1021/jo00379a020

Cited by 217 publications

(100 citation statements)

References 3 publications

(5 reference statements)

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“…Stille [5] [Pd(PPh 3 ) 4 ] (2 %), toluene, 110 8C -Fu [6] [Pd 2 (dba) 3 ] (0.5-1.5 %), PtBu 3 (1.1-3.3 %), [b] toluene or NMP, RT, (CsF, 2.2 equiv for R = Ar)…”

Section: Methodsmentioning

confidence: 99%

“…[2,3] This is more clearly seen by comparing the best current methods for the coupling of aryl bromides with Stilles original procedure published in 1987 (Table 1). [5] Fu and co-workers discovered that palladium complexes [Pd 2 (dba) 3 ]/PtBu 3 or [Pd(PtBu 3 ) 2 ], that bear bulky phosphane groups, are excellent catalysts for the coupling of aryl bromides at room temperature. [6] Verkade and co-workers developed related conditions for the Stille coupling reaction by using proazaphosphatranes as P ligands.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Couplings with Monoorganotin Compounds: A “Radical” Twist from the Original Stille Reaction

Echavarren

2005

Angew Chem Int Ed

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“…Stille [5] [Pd(PPh 3 ) 4 ] (2 %), toluene, 110 8C -Fu [6] [Pd 2 (dba) 3 ] (0.5-1.5 %), PtBu 3 (1.1-3.3 %), [b] toluene or NMP, RT, (CsF, 2.2 equiv for R = Ar)…”

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Couplings with Monoorganotin Compounds: A “Radical” Twist from the Original Stille Reaction

Echavarren

2005

Angew Chem Int Ed

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“…Synthesis of monomer 1 [26,27] Monomer 1 was synthesized according to the literatures [26,27]. 18.06 g (17.3 mmol) of 1,4-bis(bromide-triphenylphosphine methyl)-2,5-dioctyloxybenzene was dissolved in a co-solvent of 230 mL dichloromethane and 70 mL (40%) formaldehyde solution.…”

Section: Syntheses Of Monomers and Polymermentioning

confidence: 99%

A new conjugated polymer with donor-acceptor architectures based on alternating 1,4-divinyl-2,5-dioctyloxybenzene and 5,8-(2,3-dipyridyl)-quinoxaline: Synthesis, characterization, and photoinduced charge transfer

Chen¹,

Zhang²,

Gu³

et al. 2012

Express Polym. Lett.

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Abstract.A new conjugated polymer with donor-accepter architectures poly[1,4-dioctyloxyphenylene-2,5-diylethenylene-(2,3-dipyridine-2-ylquinoxaline-5,8-diyl)ethylene] (PPV-BD) was synthesized successfully, in which the electron-donating unit was alkoxy substituted phenyl ring, and the electron-accepting unit was a quinoxaline. The resulting polymer had a lower band-gap (1.98 eV) compared to poly[2-methoxy-5-(2-ethyl)hexoxy-phenylenevinylene] (MEH-PPV, 2.12 eV), and was characterized by infrared spectroscopy (IR), nuclear magnetic resonance (NMR), thermogravimetric analysis (TGA), gel permeation chromatography (GPC), ultraviolet-visible (UV-vis) spectroscopy, photoluminescence (PL) spectroscopy and X-ray diffraction (XRD). Its photoinduced charge transfer applications in polymer solar cell (PSC) and trinitrotoluene (TNT) detection were studied respectively, and the results indicated that this polymer might be a good candidate material for PSC or detecting TNT in solution.

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“…51,52) Although the preparative advantages of commercially available siloxanes are clearly demonstrated, the number of structurally diverse precursors is obviously limited. This shortcoming of such facile coupling reactions is addressed through the development of a general method for the custom preparation of alkenyl disiloxanes from simple starting materials.…”

Section: Polysiloxane Cross-couplingmentioning

confidence: 99%

Cross-Coupling Reactions of Organosilicon Compounds: New Concepts and Recent Advances.

Denmark

Sweis

2002

CHEMICAL & PHARMACEUTICAL BULLETIN

114

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Palladium-catalyzed cross-coupling reactions occupy a unique status among methods for the construction of carboncarbon bonds. The well-established Stille-Migita-Kosugi coupling of organostannanes [1][2][3] and the Suzuki-Miyaura coupling of organoboron compounds 4,5) are two reactions that, until recently, have been the "gold-standard" among various palladium-catalyzed coupling reactions. Their wide use and extraordinary synthetic utility have provided the impetus to develop newer and more effective variants (Fig. 1). More recently organosilanes have also been shown to be competent coupling partners in those reactions that employ shelf-stable reagents. The early work of Hiyama demonstrated that in the presence of a nucleophilic promoter, fluorosilanes could undergo a variety of cross-coupling reactions whose scope rivaled that of organotin and organoboron cross-couplings. [6][7][8] Since these reports, many variants of organosilicon crosscoupling have been developed that extend beyond the use of fluorosilanes and that possess many attractive features which now elevate this method to be a viable alternative to other types of cross-coupling. This report will outline recent advances in the development of organosilicon cross-coupling reactions and provide an overview of scope and applicability of this new technology.Organosilanes were previously thought to be too unreactive to be effective cross-coupling partners. The small electronegativity difference between silicon and carbon resulted in a relatively weak nucleophilic reagent for the cross-coupling. The use of fluorosilanes was therefore a significant breakthrough, demonstrating that in the presence of a nucleophilic promoter, these compounds could access a pentacoordinate "ate" species, which was postulated to undergo the coupling reaction due to its enhanced polarization at the carbon-silicon bond. Because silicon-based compounds are generally non-toxic, have low molecular weight, and are easily incorporated into molecules by a variety of methods, the potential for developing other silicon-based cross-coupling systems superior to methods previously employed was recognized.One of the first successful alternatives to fluorosilanes in organosilicon cross-coupling was achieved through the use of siletanes. Predicated on the necessity to generate a pentacoordinate silicon for the coupling process, it was hypothesized that the use of a siletane should enable generation of the pentacoordinate silicate more readily in the presence of a nucleophile due to the enhanced Lewis acidity of the silicon. This property is a manifestation of "strain release Lewis acidity" which has its origins in the difference in coordination geometry between four coordinate (tetrahedral) and five coordinate (trigonal bipyramidal) silicon species (Fig. 2). Therefore, the angle strain in a four coordinate siletane (79°vs. 109°) is partially relieved upon binding a fifth ligand to produce a trigonal bipyramidal species (79°vs. 90°) in which the siletane bridges an apical and basal position. 9,10)...

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Synthesis of functionalized styrenes via palladium-catalyzed coupling of aryl bromides with vinyl tin reagents

Cited by 217 publications

References 3 publications

Couplings with Monoorganotin Compounds: A “Radical” Twist from the Original Stille Reaction

Couplings with Monoorganotin Compounds: A “Radical” Twist from the Original Stille Reaction

A new conjugated polymer with donor-acceptor architectures based on alternating 1,4-divinyl-2,5-dioctyloxybenzene and 5,8-(2,3-dipyridyl)-quinoxaline: Synthesis, characterization, and photoinduced charge transfer

Cross-Coupling Reactions of Organosilicon Compounds: New Concepts and Recent Advances.

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