Reduction of sulfoxides and sulfilimines catalyzed by metalloporphins

Nagata, Toshiyuki; Yoshimura, Toshiaki; Fujimori, Keiya; Ōae, Shigeru

doi:10.1016/s0040-4039(00)99878-2

Cited by 14 publications

(4 citation statements)

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“…Complexes of CuCl 2 [5], CoCl 2 , and NiCl 2 [6] with triphenylphosphine and metal complexes of porphyrins such as iron meso-tetraphenylporphyrinate [ClFe(III)TPP] [7] and cobalt meso-tetra(p-sulfophenyl)porphyrinate [Co(III)TPPS] have been used successfully [8].…”

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confidence: 99%

Metal-complex catalysis during the reduction of functional groups by sodium borohydride in the synthesis of pyrrolidine derivatives

Martirosyan

Hovhanesyan

Gasparyan

et al. 2006

Chem Heterocycl Compd

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The development of selective and universal methods for the reduction of functional groups is an important function of organic chemistry.There are many ways of using the mild and readily available reducing agent sodium borohydride in various catalytic systems with the aim of extending its reducing capabilities, the selectivity of its action, and its other properties. Reducing systems containing sodium borohydride and the salts of metals, such as CuCl 2 [1], CoCl 2 [2], NiCl 2 [3], ZrCl 3 [4], and others, are well known and have been well studied. It was demonstrated that the selectivity of reduction depends on the nature of the metal. The mechanism of reduction involving the formation of borides of the respective metals has also been studied [4]. However, the method has a series of important disadvantages, mainly associated with the quantities of the reagents employed. The ratios of the compound being reduced, the metal salt, and sodium borohydride amounted to 1:2:10.The use of metal complexes as catalysts with sodium borohydride significantly simplifies the process, making it suitable for extensive application. Complexes of CuCl 2 [5], CoCl 2 , and NiCl 2 [6] with triphenylphosphine and metal complexes of porphyrins such as iron meso-tetraphenylporphyrinate [ClFe(III)TPP] [7] and cobalt meso-tetra(p-sulfophenyl)porphyrinate [Co(III)TPPS] have been used successfully [8].As catalysts for reduction in a system containing sodium borohydride we used a series of familiar metal complexes, like the complexes of CoCl 2 and CuCl 2 with triethylbenzylammonium chloride (1) and (2) [9] and cobalt and copper meso-tetra [4-(2-hydroxyethyl)pyridyl]porphyrinates (CoTOEtPyP) (3) and (CuTOEtPyP) (4)

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Metal-complex catalysis during the reduction of functional groups by sodium borohydride in the synthesis of pyrrolidine derivatives

Martirosyan

Hovhanesyan

Gasparyan

et al. 2006

Chem Heterocycl Compd

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“…3a,5 However, the reduction of sulfoxides with many reagents suffers from serious disadvantages, such as use of an expensive reagent, 5d-5f,6 difficult work-up procedures, 7 dry reaction conditions, 8 harsh acidic 9 or basic 10 conditions, low yields, 11 very high reaction temperatures, 3a,12 side products 9b and long reaction times. 13 Metal-metal salt binary systems such as Al-NiCl 2 •6H 2 O-THF, 15 Al-SbCl 3 or Zn-SbCl 3 , 16 Fe-NiCl 2 •6H 2 O-THF 17 have long been used as reducing agents for many functional groups. In this communication, the use of the Al-NiCl 2 •6H 2 O system is reported for the selective reduction of sulfoxides to sulfides in very good yields under mild conditions.…”

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“…Reduction of Sulfoxides to Sulfides All compounds were characterized by 1 H NMR,13 C NMR, IR spectroscopy and elemental analysis. reaction, the reaction mixture was diluted with EtOAc and filtered.…”

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“…The residue was washed with EtOAc several times, and the combined filtrate and washings were dried (Na 2 SO 4 ) and evaporated to dryness. Finally, the crude product thus obtained was purified by column chromatography using EtOAc and hexane as eluent and characterized by IR, NMR and elemental analysis.19 (19) Ethyl Octadecyl Sulfide: 1 H NMR (300 MHz): d = 0.88 (t, ArH) 13. C NMR (100 MHz): d = 28.42, 45.06,…”

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A Facile and Efficient Method for the Reduction of Sulfoxides into Sulfides with an Al-NiCl₂·6H₂O System

Raju¹,

Devi²,

Nongpluh³

et al. 2005

Synlett

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Cobalt, [5,10,15,20-tetraphenyl-21H,23H-porphinato(2−)-κN21,κN22,κN23,κN24]-

Singh

Collier²

2013

Encyclopedia of Reagents for Organic Synthesis

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Reduction of sulfoxides and sulfilimines catalyzed by metalloporphins

Cited by 14 publications

References 5 publications

Metal-complex catalysis during the reduction of functional groups by sodium borohydride in the synthesis of pyrrolidine derivatives

Metal-complex catalysis during the reduction of functional groups by sodium borohydride in the synthesis of pyrrolidine derivatives

A Facile and Efficient Method for the Reduction of Sulfoxides into Sulfides with an Al-NiCl₂·6H₂O System

Cobalt, [5,10,15,20-tetraphenyl-21H,23H-porphinato(2−)-κN21,κN22,κN23,κN24]-

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Reduction of sulfoxides and sulfilimines catalyzed by metalloporphins

Cited by 14 publications

References 5 publications

Metal-complex catalysis during the reduction of functional groups by sodium borohydride in the synthesis of pyrrolidine derivatives

Metal-complex catalysis during the reduction of functional groups by sodium borohydride in the synthesis of pyrrolidine derivatives

A Facile and Efficient Method for the Reduction of Sulfoxides into Sulfides with an Al-NiCl2·6H2O System

Cobalt, [5,10,15,20-tetraphenyl-21H,23H-porphinato(2−)-κN21,κN22,κN23,κN24]-

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A Facile and Efficient Method for the Reduction of Sulfoxides into Sulfides with an Al-NiCl₂·6H₂O System