- Biomimetic photocatalytic sulfonation of alkenes to access β-ketosulfones with single-atom iron site
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Biomimetic photocatalysis as an important organic transformation strategy has received increasing attention, with the performances of biomimetic catalysts largely depending on their design. This protocol has been initially used to fabricate a biomimetic photocatalyst of single-atom iron site through coupling carbon nitride with hemin (CNH) for the visible light-promoted sulfonation of alkenes to produce β-ketosulfones with up to 94% yield. The experimental results show that the role of CN in CNH is concentrated on enhancing the separation ability of photogenerated electron pairs and holes to improve the photocatalytic activity and stability. Moreover, the as-prepared photocatalyst of single atom iron can be irradiated under near-infrared light with a satisfactory yield, and is also feasible for the sulfonation reactions of androstenones. Importantly, this biomimetic catalysis-based synthesis system has some merits, namely high catalysis efficiency, favorable recyclability, high turnover number, and excellent functional group tolerance, making it promising for extensive applications in organic transformations for the synthesis of β-ketosulfones to access various bioactive drugs.
- Wen, Jiangwei,Yang, Xiaoting,Sun, Zongzhao,Yang, Jianjing,Han, Ping,Liu, Qiuxia,Dong, Hongyan,Gu, Meng,Huang, Limin,Wang, Hua
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supporting information
p. 230 - 237
(2020/01/21)
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- Palladium(II)-Catalyzed Synthesis of Sulfinates from Boronic Acids and DABSO: A Redox-Neutral, Phosphine-Free Transformation
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A redox-neutral palladium(II)-catalyzed conversion of aryl, heteroaryl, and alkenyl boronic acids into sulfinate intermediates, and onwards to sulfones and sulfonamides, has been realized. A simple Pd(OAc)2 catalyst, in combination with the sulfur dioxide surrogate 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO), is sufficient to achieve rapid and high-yielding conversion of the boronic acids into the corresponding sulfinates. Addition of C- or N-based electrophiles then allows conversion into sulfones and sulfonamides, respectively, in a one-pot, two-step process.
- Deeming, Alex S.,Russell, Claire J.,Willis, Michael C.
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supporting information
p. 747 - 750
(2016/02/27)
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- DABSO-based, three-component, one-pot sulfone synthesis
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The addition of Grignard reagents or organolithium reagents to the SO 2-surrogate DABSO generates a diverse set of metal sulfinates, suitable for direct conversion to sulfone products. The metal sulfinates can be trapped in situ with a wide range of C-electrophiles, including alkyl, allyl, and benzyl halides, epoxides, and (hetero)aryliodoniums.
- Deeming, Alex S.,Russell, Claire J.,Hennessy, Alan J.,Willis, Michael C.
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supporting information
p. 150 - 153
(2014/01/23)
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- An approach toward the synthesis of β-hydroxy sulfones on water
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Various β-hydroxyl sulfones are prepared by regioselective ring opening of epoxides with sodium salt of sulfinate on water. This is an efficient protocol which avoids hazardous and moisture sensitive catalysts.
- Narayana Murthy,Madhav,Prakash Reddy,Rama Rao,Nageswar
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scheme or table
p. 5009 - 5011
(2009/12/01)
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- Simple synthesis of β-hydroxysulfones using polysorbate-80 as phase transfer catalyst
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A very easy and practical method for the preparation of β-hydroxysulfones has been developed by ring opening of oxirane using polysorbate-80 as phase transfer catalyst.
- Maiti, A. K.,Bhattacharyya, P.
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- Polyethylene Glycol (PEG) 4000 Catalysed Regioselective Nucleophilic Ring Opening of Oxiranes - A New And Convenient Synthesis of β-Hydroxy Sulfone and β-Hydroxy Sulfide
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Oxiranes and sodium p-toluene sulfinate salt react smoothly in a regioselective manner in the presence of PEG4000 to furnish β-hydroxy sulfone and β-hydroxysulfide.The reaction was extended for the preparation of alkylsulfones and β-oxosulfones from alkylhalide and β-oxohalide respectively.
- Maiti, A. K.,Bhattacharyya, P.
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p. 10483 - 10490
(2007/10/02)
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- Regioselective ring opening of oxiranes catalysed by montmorillonite clay: A simple synthesis of β-hydroxy sulfones
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Oxiranes and sodium p-toluene sulfinate salt react smoothly in a regioselective manner in the presence of montmorillonite clay to furnish the corresponding β-hydroxy sulfones in good to excellent yield.
- Biswas,Bhattacharyya
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p. 569 - 573
(2007/10/02)
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