A facile and efficient synthesis of aryltriethoxysilanes via sonochemical Barbier-type reaction

Lee, Adam Shih‐Yuan; Chang, Yu‐Ting; Chu, Shu‐Fang; Tsao, Kuo-Wei

doi:10.1016/j.tetlet.2006.07.078

Cited by 23 publications

(3 citation statements)

References 30 publications

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“…POP was purified by a combination of short‐path and multi‐tray distillation processes to greater than 99% purity by gas chromatography analysis. The PSP monomer was synthesized in 89% crude yield by a Barbier‐style reaction, which proved to be a simpler and more reliable procedure for both monomers. PSP was purified to 96% purity via short‐path distillation.…”

Section: Resultsmentioning

confidence: 99%

High refractive index thermally stable phenoxyphenyl and phenylthiophenyl silicones for light‐emitting diode applications

Mosley

Khanarian

Conner

et al. 2013

J of Applied Polymer Sci

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Creating high refractive index (RI) thermally stable polymers for encapsulating high‐brightness light‐emitting diodes (LEDs) remains a challenge and is an opportunity for improving LED efficiencies. The best previously reported RI for a 200°C heat stable encapsulant for LEDs is 1.56. Here, we report the use of novel phenoxyphenyl and phenylthiophenyl silicone monomers to give fully formulated encapsulants with RIs above 1.60. These liquid dispensed encapsulants are highly heat stable, showing little change in optical properties after heat aging at 200°C in air for seven weeks, and were also little changed after cycling between −10°C to 85°C over 6 months. Phenoxyphenyl(phenyl) dimethoxysilane and phenylthiophenyl(phenyl) dimethoxysilane monomers were prepared via Grignard reactions. The resulting monomers were copolymerized with commercial silicone monomers and incorporated into hydrosilation‐based thermosets designed for use as LED encapsulants. RIs for the cured polymers were 1.60 at 633 nm (1.62 at 450 nm) for the phenoxyphenyl ether system and 1.62 at 633 nm (1.65 at 450 nm) for the phenylthiophenyl ether system. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 39824.

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Section: Resultsmentioning

confidence: 99%

High refractive index thermally stable phenoxyphenyl and phenylthiophenyl silicones for light‐emitting diode applications

Mosley

Khanarian

Conner

et al. 2013

J of Applied Polymer Sci

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“…Several methods are available to make arylsilanes: Transmetalation from aryl Grignard reagents to tetraalkoxysilanes provides aryl silanes. 13 For molecules that contain functional groups that are not compatible with Grignard reagents, Pd(0)- or Rh(I)-catalyzed silylation of aryl iodides and bromides with tetraethoxysilanes can afford aryl silanes. 14 …”

Section: Introductionmentioning

confidence: 99%

Silver-mediated fluorination of aryl silanes

2011

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“…The limits of our early attempts toward benzylic silanediol synthesis prompted us to explore more uncommon benzylic C(sp 3 )−Si bond forming reaction conditions that may afford us higher yields and/or be more tolerant of the functional groups on both of the reaction partners. The results of our own experimentation, working in combination with Lee and coworkers' demonstration of the power of sonication in aryl− silicon bond formation, 6 encouraged us to pursue Barbier-type reaction conditions to establish the desired C−Si bond. We were delighted to find that Barbier-type coupling of benzylic bromide 2 (X = Br) and phenylchlorosilane 3 gave rise to desired silane 1a in 94% yield (Table 1).…”

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confidence: 99%

Carbon–Silicon Bond Formation in the Synthesis of Benzylic Silanes

2016

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Sterically encumbered organosilanes can be difficult to synthesize with conventional, strongly basic reagents; the harsh reaction conditions are often low yielding and not suitable for many functional groups. As an alternative to the typical anionic strategies to construct silanes, the coupling of benzylic halides and arylhalosilanes with sonication has been identified as a high yielding and general strategy to access bulky and functionalized benzylic silanes. This new methodology provides a solution for the synthesis of families of bulky benzylic silanes for study in catalysis and other areas of chemical synthesis.

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A facile and efficient synthesis of aryltriethoxysilanes via sonochemical Barbier-type reaction

Cited by 23 publications

References 30 publications

High refractive index thermally stable phenoxyphenyl and phenylthiophenyl silicones for light‐emitting diode applications

High refractive index thermally stable phenoxyphenyl and phenylthiophenyl silicones for light‐emitting diode applications

Silver-mediated fluorination of aryl silanes

Carbon–Silicon Bond Formation in the Synthesis of Benzylic Silanes

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