Synthesis of α-Arylated Phenylsulfonylacetonitriles. A Useful Precursor for Substituted α-Arylalkanoic Acid and Their Derivatives

Suzuki, Hitomi; Yi, Qui; Inoue, Jinya; Kusume, K.; Ogawa, Takuji

doi:10.1246/cl.1987.887

Cited by 29 publications

(17 citation statements)

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“…In these studies, we demonstrated that photolysis of these arylated ethyl cyanoacetate or phenylsulphonylacetonitrile complexes led to the liberation of the compounds from their metal moieties in very high yields. These compounds are very valuable precursors to alkanoic acids and heterocyclic compounds that are known for their great importance in the pharmaceutical industry (22)(23)(24)(25)(26)(27)(28). One of the most important alkanoic acids is 2-(4-isobutylpheny1)propanoic acid, which is widely known as Ibuprofen.…”

Section: Introduction Matic Compounds Our Research Interest Is Focusmentioning

confidence: 99%

“…hydes followed by oxidation to give the alkanoic acids (35, arylation of phenylsulphonylacetonitriles, which are converted to alkanoic acids via alkylation and reductive desulphonation, followed by hydrolysis (25). This synthesis allows for the introduction of alkyl groups after the arylation of phenylsulphonylacetonitrile.…”

Section: Introduction Matic Compounds Our Research Interest Is Focusmentioning

confidence: 99%

“…This synthesis allows for the introduction of alkyl groups after the arylation of phenylsulphonylacetonitrile. To date there are few reports on the synthesis of arylated phenylsulphonylacetonitriles that have been shown to be converted to alkanoic acids (25,37,38). Suzuki et al have shown that arylation of phenylsulphonylacetonitrile could be achieved via the displacement of an iodo group of an aryl iodide using a carbon nucleophile (25).…”

Section: Introduction Matic Compounds Our Research Interest Is Focusmentioning

confidence: 99%

“…To date there are few reports on the synthesis of arylated phenylsulphonylacetonitriles that have been shown to be converted to alkanoic acids (25,37,38). Suzuki et al have shown that arylation of phenylsulphonylacetonitrile could be achieved via the displacement of an iodo group of an aryl iodide using a carbon nucleophile (25). This nucleophile was generated from the reaction of phenylsulphonylacetonitrile and sodium hydride in the presence of a copper salt as catalyst and HMPA as solvent.…”

Section: Introduction Matic Compounds Our Research Interest Is Focusmentioning

confidence: 99%

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Ironcyclopentadienyl mediated 2-alkyl-2-arylphenylsulphonylacetonitrile synthesis

Abd‐El‐Aziz¹,

Denus²,

Hutton³

1995

Can. J. Chem.

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Abstract:A unique route to the synthesis of 2-alkyl-2-arylphenylsulphonylacetonitriles via the nucleophilic aromatic substitution (SNAr) of chloroarene cyclopentadienyliron complexes with 2-alkyl phenylsulphonylacetonitriles has been investigated. Reactions of chloroarene complexes (la-6) with 2-alkyl phenylsulphonylacetonitrile (2a,b) in the presence of K,CO, in DMF at room temperature led to the formation of complexes 3a-d and 4a,c,d in good yields. The use of alkylated phenylsulphonylacetonitriles as nucleophiles in the reactions with thep-dichlorobenzene complex ( l e ) allowed the formation of the disubstituted complexes (5,6). Photolytic demetallation provided an efficient route to the liberation of the arylated phenylsulphonylacetonitriles 7a-d, 8a,c,d, 9, and 10.Key words: chloroarene, phenylsulphonylacetonitrile, nucleophilic substitution.RCsumC : On explore une mtthode originale de synthbse des 2-alkyl-2-arylphCnylsulphonylacCtonitriles via la substitution aromatique nuclCophile (SNAr) des complexes du chloroarbnecyclopentadiCnyl de fer avec les 2-alkylphCnylsulphonylacCtonitriles. Les rkactions des complexes de choroarbnes (10-6) avec le 2-alkylphCnylsulphonylacCtonitrile (2a,b) en presence de K,CO, dans le DMF a la temperature ambiante conduisent, avec de bons rendements, ? i la formation des complexes 3a-d et 4a,c,d. L'emploi des phCnylsulphonylacCtonitriles alkyICs comme nuclCophiles dans la reaction avec le complexe de p-dichlorobenzbne ( l e ) permet la formation de complexes disubstituCs ( 5 , 6 ) . La dCmCtallation photolytique foumit une excellente voie d'acces a la liberation des phCnylsulphonylacCtonitriles 7a-d, 8a,c,d, 9 et 10.

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Section: Introduction Matic Compounds Our Research Interest Is Focusmentioning

confidence: 99%

Section: Introduction Matic Compounds Our Research Interest Is Focusmentioning

confidence: 99%

Section: Introduction Matic Compounds Our Research Interest Is Focusmentioning

confidence: 99%

Section: Introduction Matic Compounds Our Research Interest Is Focusmentioning

confidence: 99%

See 2 more Smart Citations

Ironcyclopentadienyl mediated 2-alkyl-2-arylphenylsulphonylacetonitrile synthesis

Abd‐El‐Aziz¹,

Denus²,

Hutton³

1995

Can. J. Chem.

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“…[35,36] This copper(I)-catalyzed coupling reaction is best carried out with aryl iodides. Frequently, a stoichiometric amount of copper(I) salt is necessary for reasonable yields.…”

Section: Decarboxylation Of Malonic Acids Their Monoesters and Cyanomentioning

confidence: 99%

Naproxen Derivatives by Enantioselective Decarboxylation

Brunner

Schmidt

2000

Eur. J. Org. Chem.

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Desulfonylation Reactions

Alonso

Ájera

2009

Organic Reactions

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The use of sulfones in organic chemistry, acting as an auxiliary group, is still a very important synthetic strategy, especially for the formation of carbon‐carbon single and double bonds. Once the synthetic objective is achieved, the sulfone gruop is usually removed from the molecule. This removal most commonly involves a reductive desulfonylation process with either replacement of the sulfone by hydrogen, or a process that results in the formation of a carbon‐carbon double bond when a β‐hydroxy or β‐alkoxy sulfone is employed. This chapter is devoted to the replacement of the sulfone group by a hydrogen (reductive desulfonylation reactions), and reductive elimination reactions of Julia‐type substrates (Julia‐Lythgoe olefination process). The chapter addresses the full scope, generality, limitations, and synthetic applications of these reactions. The literature through most of 2007 is covered.

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Synthesis of α-Arylated Phenylsulfonylacetonitriles. A Useful Precursor for Substituted α-Arylalkanoic Acid and Their Derivatives

Cited by 29 publications

References 6 publications

Ironcyclopentadienyl mediated 2-alkyl-2-arylphenylsulphonylacetonitrile synthesis

Ironcyclopentadienyl mediated 2-alkyl-2-arylphenylsulphonylacetonitrile synthesis

Naproxen Derivatives by Enantioselective Decarboxylation

Desulfonylation Reactions

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