Silicon directed ipso-substitution of polymer bound arylsilanes: Preparation of biaryls via the Suzuki cross-coupling reaction

Han, Yongxin; Walker, Shawn D.; Young, Robert N.

doi:10.1016/0040-4039(96)00364-4

Cited by 122 publications

(73 citation statements)

References 23 publications

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“…High yields were obtained, however, in DMF/NEt 3 (1:1) and in the presence of [Pd(PPh 3 ) 4 ]. [22] Subsequent oxidation with NBS in the presence of pyridine and methanol-induced fragmentation of the intermediary formed diazene (Method D) delivered fluorinated biaryl compound 61 in a very useful overall yield of 55 %.…”

Section: Compoundmentioning

confidence: 99%

“…Polystyrene-bound acid (22): To a suspension of the polystyrene-bound aldehyde 21 (4.0 g, 3.28 mmol) in 1,2-dichloroethane/cyclohexane (1:1, 160 mL) was added m-chloroperbenzoic acid (m-CPBA, 70 %, 8.1 g, 32.8 mmol) and the mixture was refluxed for 48 h. After cooling to room temperature, the mixture was filtered. The resin was washed with methylene chloride, THF, THF/1n HCl (1:1), methanol, methylene chloride, and cyclohexane (2 Â each), and then dried to constant weight in vacuo to yield the off-white resin 22 (3.98 g).…”

mentioning

confidence: 99%

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Development of the Traceless Phenylhydrazide Linker for Solid‐Phase Synthesis

Stieber¹,

Grether²,

Waldmann³

2003

Chemistry A European J

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The hydrazide group is a new oxidatively cleavable traceless linker for solid-phase chemistry. It can be readily introduced by hydrazide formation between a carboxy-functionalized resin and different substituted hydrazines. In order to achieve high yields in this step, new carboxylic acid resins were developed that are not prone to undesired imide formation upon activation of the carboxylic acid. The polymer-bound acyl hydrazides were successfully employed in various transformations, namely Heck, Suzuki, Sonogashira, and Stille couplings, as well as Wittig and Grignard reactions. Traceless release of the coupling products from the solid support is achieved selectively under mild conditions and in high purity by oxidation of the aryl hydrazides to acyl diazenes with Cu(II) salts or N-bromosuccinimide (NBS) and subsequent nucleophilic attack of the acyl diazene intermediates. Traceless cleavage by oxidation with NBS can be carried out as a two-step process in which stable acyl diazenes are first generated by treatment with NBS in the absence of a nucleophile. After removal of the reagents by simple resin washing, the traceless release is effected by the addition of methanol, which leads to products of high purity without any additional separation steps.

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Section: Compoundmentioning

confidence: 99%

mentioning

confidence: 99%

Development of the Traceless Phenylhydrazide Linker for Solid‐Phase Synthesis

Stieber¹,

Grether²,

Waldmann³

2003

Chemistry A European J

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“…The key intermediate (4-bromophenyl)-chloromethyldimethylsilane (1) was prepared from para-dibromobenzene via metalation with butyl lithium and by the reaction of the intermediate, formed chloromethyl-dimethylsilyl chloride [10,11]. Chloromethylsilyl derivative 1 was then reacted with imidazole in the presence of one equivalent of triethylamine at 120 °C under MW in the absence of any solvent to give imidazolylmethylsilyl derivative (2).…”

Section: Resultsmentioning

confidence: 99%

Suzuki–Miyaura Reaction of 4-Silyl-bromobenzenes with Phenylboronic Acid under Thermal and Microwave Conditions

Greiner¹,

Hohmann²,

Vida³

et al. 2008

TOOCJ

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Abstract:The coupling reaction of phenylboronic acid with 4-silyl-bromobenzenes incorporating an ionic liquid support or its neutral analogue at 80 °C in DMF/H 2 O in the presence of Pd(PPh 3 ) 4 and Na 2 CO 3 takes place much faster and more efficiently under microwave irradiation than under traditional heating. It is an attractive method to carry out the generally slow Suzuki-Miyaura reactions under microwave conditions.

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“…Most of the developed linkers that allow multidirectional electrophilic cleavage from the resin are based on the chemistry of silicon and also to a less extent on germanium [140][141][142]. Silyl linkers have broad appeal in solid-phase synthesis.…”

Section: Direct Cleavage By Electrophilesmentioning

confidence: 99%

Solid Phase and Combinatorial Chemistry in the Heterocyclic Field

Villalgordo¹

2011

Modern Heterocyclic Chemistry

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Silicon directed ipso-substitution of polymer bound arylsilanes: Preparation of biaryls via the Suzuki cross-coupling reaction

Cited by 122 publications

References 23 publications

Development of the Traceless Phenylhydrazide Linker for Solid‐Phase Synthesis

Development of the Traceless Phenylhydrazide Linker for Solid‐Phase Synthesis

Suzuki–Miyaura Reaction of 4-Silyl-bromobenzenes with Phenylboronic Acid under Thermal and Microwave Conditions

Solid Phase and Combinatorial Chemistry in the Heterocyclic Field

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