A New Effective Synthesis of Arene Mono- and Disulfonyl Chlorides

Barbero, Margherita; Bazzi, Stefano; Cadamuro, Silvano; Dughera, Stefano; Magistris, Claudio; Venturello, Paolo

doi:10.1055/s-0030-1258104

Cited by 19 publications

(12 citation statements)

References 12 publications

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“…Barbero et al reported a synthesis of (R)-1,1'-binaphthyl-2,2'-disulfonyl chloride ((R)-10) from commercially available (R)-1,1'-binaphthyl-2,2'-diamine ((R)-11) (Scheme 4). [14] This approach began by the diazotization of (R)-11, and the corresponding diazonium tetrafluoroborate (R)-12 was isolated. Compound (R)-12 was treated with KSCSOEt in acetonitrile to give the xanthate (R)-13.…”

Section: Synthesis Of Optically Pure Binsasmentioning

confidence: 99%

Chiral 1,1′‐Binaphthyl‐2,2′‐Disulfonic Acid (BINSA) and Its Derivatives for Asymmetric Catalysis

Hatano

Ishihara

2014

Asian J Org Chem

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Chiral Brønsted acid catalysts, which are derived from commercially available (R)-or (S)-1,1'-bi-2-naphthol (BINOL), have found widespread application as chiral organocatalysts and chiral ligands for metal species. The Brønsted acidity of these catalysts is considered to be associated with their catalytic activity. Therefore, due to the rapid development of asymmetric organocatalysis, chiral 1,1'-binaphthyl-2,2'-disulfonic acid (BINSA) and the corresponding chiral binaphthyl disulfonimides are highly attractive as stronger chiral Brønsted acid catalysts than carboxylic acids, phosphoric acids, and phosphoramides. This Focus Review summarizes the latest achievements in chiral BINSA chemistry, particularly in the field of asymmetric organocatalysis.Keywords: asymmetric catalysis · 1,1'-binaphthyl-2,2-disulfonic acids · Brønsted acids · organocatalysis · sulfonic acids[a] Dr.

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Section: Synthesis Of Optically Pure Binsasmentioning

confidence: 99%

Chiral 1,1′‐Binaphthyl‐2,2′‐Disulfonic Acid (BINSA) and Its Derivatives for Asymmetric Catalysis

Hatano

Ishihara

2014

Asian J Org Chem

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“…The chemistry of these systems has seen fair less investigation than those based upon the 1,2-benzene scaffold. A number of reports have been published describing the synthesis of simple thioether compounds (D), [8][9][10][11] (E) [12,13] and (F) [14] (Figure 2). However, to date there has been no report of the acenaphthene derivative.…”

Section: Introductionmentioning

confidence: 99%

“…The work conducted by Barbero, which describes the synthesis of E, was examining synthetic routes to arene mono-and disulfonyl chlorides which are key intermediates for the synthesis of strong Brønsted acids which are useful organocatalysts. [13] Longer chain alkyl groups have also been utilised including ethyl derivatives of naphthalene (G) [15] and biphenyl (H) [12] as well as a butyl analogue on naphthalene (I) [16] (Figure 2). Figure 3 (J-M) shows the phenyl analogues that have been prepared based upon these backbones.…”

Section: Introductionmentioning

confidence: 99%

Bis (alkyl)thioethers on a biphenyl scaffold: A spectroscopic and structural insight

Ferguson

Nejman

Slawin

et al. 2017

Journal of Molecular Structure

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A series of bis(alkyl)thioether compounds utilising biphenyl as the backbone of the type 2,2′-bis(alkylthio)-1,1′-biphenyl have been prepared with yields of 32-70%. The six benzyl derivatives all displayed an AB quartet for the CH2 hydrogens within their 1 H NMR spectra due to restricted rotation within the molecule. Where the alkyl group was changed to neopentyl the CH2 protons became equivalent giving rise to a singlet within the 1 H NMR spectrum. The compounds have been characterised principally using multinuclear NMR spectroscopy and single crystal X-ray diffraction.

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“…Not surprisingly, the corresponding cyclic aryl-sulfonimide, o-benzenesulfonimide, 25 worked similarly to dibenzenesulfonimide. As shown in Table 1, o-benzenesulfonimide was able to open the aryl-, alkyl-, and heteroaryl-oxazoline rings on substrates 1, 3, 8, 9, and 11, respectively, with yields ranging from 72% to 95%.…”

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confidence: 97%

Sulfonimidation via ring-opening of 2-oxazolines with acidic sulfonimide nucleophiles

Gutiérrez¹,

Dean²,

Laxamana³

et al. 2016

Arkivoc

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Acidic sulfonimide nucleophiles including dibenzenesulfonimide, o-benzenesulfonimide, dimethanesulfonimide, and N-(methylsulfonyl)-benzenesulfonamide are discovered to open a variety of alkyl-, aryl-and heteroaryl-2-oxazoline rings to provide the sulfonimidation products in refluxing 1,4-dioxane. The electron-rich 2-oxazoline substrates worked well for the nucleophilic ring-opening reactions while no reaction took place for the electron-poor 2-oxazoline substrates.

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A New Effective Synthesis of Arene Mono- and Disulfonyl Chlorides

Abstract: Arene mono-and disulfonyl chlorides have been easily synthesized starting from the corresponding anilines via aqueous oxidative chlorination of S-aryl O-ethyl dithiocarbonates intermediates, aryl methyl sulfides, or from arenethiols.

Cited by 19 publications

References 12 publications

Chiral 1,1′‐Binaphthyl‐2,2′‐Disulfonic Acid (BINSA) and Its Derivatives for Asymmetric Catalysis

Chiral 1,1′‐Binaphthyl‐2,2′‐Disulfonic Acid (BINSA) and Its Derivatives for Asymmetric Catalysis

Bis (alkyl)thioethers on a biphenyl scaffold: A spectroscopic and structural insight

Sulfonimidation via ring-opening of 2-oxazolines with acidic sulfonimide nucleophiles

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