Metal-Free Synthesis of Diaryl Sulfones from Arylsulfinic Acid Salts and Diaryliodonium Salts

Umierski, Natalie; Manolikakes, Georg

doi:10.1021/ol303248h

Cited by 158 publications

(70 citation statements)

References 55 publications

(13 reference statements)

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“…in good yields from the reactions of diaryliodonium salts 3 and arenesulfinate salts 4 in DMF at 90°C within 24 hours. 28 However, these reaction conditions failed to produce alkyl sulfones 5m-p which were successfully prepared in good yields under the present reaction conditions. Further, our rapid protocol (10 min vs. 24 h) utilizes only a small amount of biodegradable PEG-400 (100 μL) and avoids the use of DMF.…”

Section: Scheme 1 Comparison Of Previous Work and This Workmentioning

confidence: 64%

A Metal-Free and Microwave-Assisted Efficient Synthesis of Diaryl Sulfones

Kumar¹,

Arun²,

Pilania³

et al. 2013

Synlett

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An efficient and general protocol for the synthesis of diaryl sulfones via the metal-free coupling of readily available diaryliodonium salts and arenesulfinates in PEG-400 under microwave irradiation has been developed. Utilizing this metal-free and ecofriendly protocol, we have prepared various diaryl sulfones in high yields and shorter reaction times under mild conditions. Furthermore, the coupling of diaryliodonium with arenesulfinate salts with and without copper iodide provides a convenient access to various diaryl sulfones with high selectivity.

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Section: Scheme 1 Comparison Of Previous Work and This Workmentioning

confidence: 64%

A Metal-Free and Microwave-Assisted Efficient Synthesis of Diaryl Sulfones

Kumar¹,

Arun²,

Pilania³

et al. 2013

Synlett

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“…of Ph 2 I + PF 6 À , and 2 equiv. of Et 3 N, leading to the formation of the expected olefin 3a in 52 % yield of isolated product ( (4), likely arising from the reaction between the released PhSO 2 group from bissulfone 2 and Ph 2 I + , PF 6 À , [30] indicating that a part of the iodonium reagent was consumed in undesired processes. The reaction was thus repeated using an excess of Ph 2 I + , PF 6 À (3 equiv.)…”

Section: Resultsmentioning

confidence: 99%

Aryl Radical‐Mediated Alkenylation of Alkyl Halides

Chaambi

Kurtay

Abderrahim

et al. 2019

Helvetica Chimica Acta

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The free‐radical alkenylation of a range of alkyl iodides with a vinyldisulfones has been carried out, leading to the desired vinylsulfones in moderate to good yields under mild conditions. The process is initiated by an aryl radical which abstracts the iodine atom from the alkyl iodide to form a C‐centered radical intermediate, the addition of which onto the vinyldisulfone providing the final vinylsulfone. The aryl radical is generated in situ through a single‐electron transfer from an electron donor‐acceptor complex (EDA) formed between a diaryliodonium salt (Ph2I+ PF6−) and triethylamine.

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“…Finally, we explored the coupling procedure utilising other sodium aryl sulfinate salts. Both electron-rich and electrondeficient arylsulfinates react with bromobenzene efficiently (entries [10][11][12][13][14]. The sterically hindered sodium arylsulfinates react slowly with bromobenzene to give the corresponding products (entries [15][16][17].…”

Section: Resultsmentioning

confidence: 99%