Iron-catalyzed aromatic sulfuration with sulfenyl chlorides

Fujisawa, Tamotsu; Kobori, Takeo; Ohtsuka, Noriko; Tsuchihashi, Gen-ichi

doi:10.1016/s0040-4039(00)72287-8

Cited by 23 publications

(3 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…: 54–56 °C (lit. 57–58 °C); 1 H NMR (400 MHz, CDCl 3 ) δ =3.81 (s, 3 H), 6.69–6.71 (m, 1 H), 6.93 (d, J =8.8 Hz, 2 H), 6.99–7.02 (m, 2 H), 7.29–7.31 (m, 1 H), 7.44 ppm (d, J =8.8 Hz, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ =55.3, 115.3, 121.4, 125.9, 127.0, 127.3, 129.3, 130.8, 136.8, 138.7, 160.4 ppm; HRMS (EI) m / z calcd for C 13 H 11 ClOS (M) + 250.0219, found: 250.0217.…”

Section: Methodsmentioning

confidence: 99%

Para‐Selective C−H Thioetherification

Hsu

Lee

2017

Asian J Org Chem

View full text Add to dashboard Cite

We reportt he synthesis of thioether with high regioselectivity.T he reaction proceeds through regioselective brominationf ollowed by ac opper/oxalicd iamide-catalyzed CÀSb ond cross-coupling reaction. Functional groups, such as fluoro, chloro, trifluoromethyl, nitro, unprotecteda mine and pyridine, are tolerated by the reaction conditions. Scheme2.Scope of thiols with anisole.Scheme3.Scopeo fa reneswith thiols.Scheme4.Scopeo fp henol and aniline with thiols.Scheme5.Plausible mechanism for para-selectiveC ÀHt hioetherification.

show abstract

Section: Methodsmentioning

confidence: 99%

Para‐Selective C−H Thioetherification

Hsu

Lee

2017

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

“…They can be synthesized under very mild conditions at room temperature by means of the photo-Fries rearrangement in moderate-to-good yields. The present experimental conditions are advantageous over the thermal Fries rearrangement, where higher temperatures (80 -1208) and Lewis acid catalysts such as AlCl 3 2.5. Photophysical Considerations.…”

Section: Photo-fries Rearrangement In Solutionmentioning

confidence: 99%

Photo‐Fries Rearrangement of Carbazol‐2‐yl Sulfonates: Efficient Tool for the Introduction of Sulfonyl Groups into Polycyclic Aromatic Compounds

Crevatín

Bonesi

Erra‐Balsells

2006

Helvetica Chimica Acta

View full text Add to dashboard Cite

Systematic studies on the photo-Fries rearrangement of different 9H-carbazol-2-yl sulfonates 2 have shown that this type of conversion can be readily used for the preparative-scale introduction of alkyl-or arylsulfonyl groups into polycyclic aromatic compounds under very mild conditions. A series of new 1-sulfonyl-(3) or 3-sulfonyl-9H-carbazoles (4) were prepared in medium-to-good yields, and characterized by UV/VIS, 1 H-NMR, and 13 C-NMR spectroscopy, as well as by elemental analysis. Effects of irradiation wavelength, solvent polarity, presence or absence of O 2 , and photosensitizers were studied in detail.

show abstract

“…For example, anisole, mxylene, and diphenyl ether are sulfenylated with benzenesulfenyl chloride in the presence of iron powder in the dark [5]. The reaction of 1-phenylpyrazole with o-nitrobenzenesulfenyl chloride proceeds without catalysis under refluxing in ethylene dichloride [6].…”

Section: Introductionmentioning

confidence: 99%