- Synthesis of β-Keto Sulfones via Coupling of Aryl/Alkyl Halides, Sulfur Dioxide and Silyl Enolates through Metal-Free Photoinduced C–X Bond Dissociation
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A photoinduced sulfonylative coupling of aryl/alkyl halides, DABCO?(SO2)2 (1,4-diazabicyclo[2.2.2]octane-sulfur dioxide), and silyl enolates under metal-free conditions has been developed, giving rise to β-keto sulfones in good yields. This transformation proceeds smoothly at room temperature under ultraviolet irradiation with good tolerance of various functional groups. Aryl iodides/bromides and alkyl halides are all good substrates in the sulfonylative reaction. A plausible mechanism is proposed, which proceeds through a radical process under photoinduced conditions. (Figure presented.).
- Gong, Xinxing,Ding, Yechun,Fan, Xiaona,Wu, Jie
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supporting information
p. 2999 - 3004
(2017/09/08)
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- Oxysulfonylation of Alkenes with Sulfonyl Hydrazides under Transition-Metal-Free Conditions
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A novel method to synthesise β-keto sulfones is demonstrated by Br?nsted acid promoted oxysulfonylation of alkenes with sulfonyl hydrazides under transition-metal-free conditions. The reaction selectively affords structurally diverse β-keto sulfones in good to excellent yields in a 9:1 mixture of acetonitrile/water.
- Liu, Congrong,Ding, Lianghui,Guo, Guang,Liu, Weiwei
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p. 910 - 912
(2016/03/01)
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- Aerobic oxidation in nanomicelles of aryl alkynes, in water at room temperature
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On the basis of the far higher solubility of oxygen gas inside the hydrocarbon core of nanomicelles, metal and peroxide free aerobic oxidation of aryl alkynes to β-ketosulfones has been achieved in water at room temperature. Many examples are offered that illustrate broad functional group tolerance. The overall process is environmentally friendly, documented by the associated low E Factors. It's all happenin' in the micelle! The highly preferential dissolution of oxygen gas within the lipophilic cores inside nanomicelles leads to efficient trapping of in situ generated vinyl radicals. These intermediate radicals, derived from arylalkynes and sulfinic acids, lead to β-ketosulfone products, formed under especially mild and green conditions: no metals, no heating or cooling, recyclable aqueous media, and low E Factors.
- Handa, Sachin,Fennewald, James C.,Lipshutz, Bruce H.
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supporting information
p. 3432 - 3435
(2014/04/03)
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- Sulfonation and trifluoromethylation of enol acetates with sulfonyl chlorides using visible-light photoredox catalysis
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A mild, practical method to prepare α-sulfonyl and α-trifluoromethyl ketones from readily available enol acetates and sulfonyl chlorides has been developed using visible-light photoredox catalysis. The method could be used with a wide range of enol acetates and sulfonyl chlorides, and gave the desired products in satisfactory to excellent yields. A practical method to prepare α-sulfonyl and α-trifluoromethyl ketones from enol acetates and sulfonyl chlorides using visible-light photoredox catalysis is presented. Copyright
- Jiang, Heng,Cheng, Yuanzheng,Zhang, Yan,Yu, Shouyun
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supporting information
p. 5485 - 5492
(2013/09/02)
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- Dioxygen-triggered oxidative radical reaction: Direct aerobic difunctionalization of terminal alkynes toward β-keto sulfones
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An unprecedented dioxygen-triggered oxidative radical process was explored using dioxygen as the solely terminal oxidant, realizing aerobic oxidaitve difunctionalization of terminal alkynes toward β-keto sulfones with high selectivity. Operando IR experiments revealed that pyridine not only acts as a base to successfully surpress ATRA (atom transfer radical addition) process, but also plays a vital role in reducing the activity of sulfinic acids.
- Lu, Qingquan,Zhang, Jian,Zhao, Ganglu,Qi, Yue,Wang, Huamin,Lei, Aiwen
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supporting information
p. 11481 - 11484
(2013/09/02)
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