The synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones

Procter, David J.

doi:10.1039/b002081h

Cited by 182 publications

(55 citation statements)

References 572 publications

(213 reference statements)

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“…The enantioselective oxidation of prochiral sulfides is one of the most efficient and practical procedures to achieve optically active sulfoxides, [1][2][3][4][5] compounds of great synthetic interest as chiral auxiliaries, 6 synthetic intermediates and bioactive compounds. 7 Enantioselective oxidations of sulfides can be performed either by biocatalysis 8,9 or by chemical oxidation, the latter occurring in the presence of chiral oxidizing species, or by using achiral oxidants and chiral metal complexes.…”

Section: Introductionmentioning

confidence: 99%

“…7 Enantioselective oxidations of sulfides can be performed either by biocatalysis 8,9 or by chemical oxidation, the latter occurring in the presence of chiral oxidizing species, or by using achiral oxidants and chiral metal complexes. [1][2][3][4][5]7 The most successful enantioselective oxidation procedure, which also has industrial application, [10][11][12][13] requires the use of achiral hydroperoxides in the presence of stoichiometric amounts of a chiral Ti(IV) complex. This approach dates back to the seminal work of Kagan and coworkers [14][15][16][17] and Modena and coworkers 18 who, independently, reported the use of alkyl hydroperoxides in conjunction with a stoichiometric amount of a Ti-complex formed in situ from Ti (i-PrO) 4 and (R,R)-diethyl tartrate (DET).…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective oxidation of sulfides catalyzed by titanium complexes of 1,2‐diarylethane‐1,2‐diols: Effect of the aryl substitution

et al. 2008

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The effects of the substitution on the aryl moiety on the asymmetric oxidation of sulfides mediated by Ti-complexes of chiral 1,2-diarylethane-1,2-diols were investigated. The substitution of the aryl ring of the diol with both EWG and EDG substituents generally decreased the enantioselectivity with respect to the use of unsubstituted 1,2-diphenylethane-1,2-diol (1a). Only in the presence of 1,2-di(4-t-butyl)phenyl-1,2-diol (1g) were higher ee's obtained with aryl methyl and aryl benzyl sulfides affording ee's up to 90 and 99%, respectively. Lower ee's were achieved with larger naphthyl and aryl alkyl sulfides. Contrary to the other Ti-alcoholates used in the oxidation of sulfides, the Ti-complex of diol 1g was soluble in hexane, allowing us to perform the process with high enantioselectivity in this solvent, with great environmental advantages over the commonly used chlorinated solvents.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantioselective oxidation of sulfides catalyzed by titanium complexes of 1,2‐diarylethane‐1,2‐diols: Effect of the aryl substitution

et al. 2008

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“…[1][2][3][4] The transition metal catalyzed cross-coupling reactions offer a powerful strategy for the construction of aryl-sulfur bonds. This approach involves the coupling of organic halides with thiols.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in copper-catalyzed C-S cross-coupling reactions

Asha¹,

Thomas²,

Thankachan³

et al. 2014

Arkivoc

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Copper-catalyzed cross-coupling reactions offer a powerful tool for the formation of carbonheteroatom bonds. Copper catalysis has an indisputable advantage over the other catalytic systems due to its low cost and the use of readily accessible and stable ligands. Among the various copper-catalyzed coupling reactions, C-S bond forming reactions have gained much attention due to its applications in the synthesis of molecules having biological and pharmaceutical impact. This review illustrates the current strategies and applications of Cucatalyzed C-S cross coupling reactions.

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“…[10][11][12][13] As a result, the preparation of diaryl sulfides has caught a great attention. [14][15][16][17] Various traditional methods such as Chan-Lam coupling, Leuckart thiophenol reaction, Sandmeyer-type reaction through diazonium salts, and Ullmann reaction can form aryl-sulfur bonds. Although moderate to high yields can be obtained, often harsh reaction conditions or long reaction times are needed in these methods.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Cross‐Coupling for the Construction of Diaryl Sulfides

Tan

Chen

et al. 2011

J Chinese Chemical Soc

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The construction of diaryl sulfides through the cross-coupling of aryl iodides and thiols in microwave heating is described. By using this method, a variety of diaryl sulfides can be prepared in a mild condition and in high yields. Deactivated 4-nitrothiophenol was effective to afford the product in 94% yield. Sterically hindered ortho-substituted aryl iodides or thiophenols provided diaryl sulfides effectively by this microwave-assisted coupling reaction.

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The synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones

Cited by 182 publications

References 572 publications

Enantioselective oxidation of sulfides catalyzed by titanium complexes of 1,2‐diarylethane‐1,2‐diols: Effect of the aryl substitution

Enantioselective oxidation of sulfides catalyzed by titanium complexes of 1,2‐diarylethane‐1,2‐diols: Effect of the aryl substitution

Recent advances in copper-catalyzed C-S cross-coupling reactions

Microwave‐Assisted Cross‐Coupling for the Construction of Diaryl Sulfides

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