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Literature DB >> 28370917

Palladium-Catalyzed Fluorosulfonylvinylation of Organic Iodides.

Gao-Feng Zha¹, Qinheng Zheng², Jing Leng¹, Peng Wu³, Hua-Li Qin¹, K Barry Sharpless².

Abstract

A palladium-catalyzed fluorosulfonylvinylation reaction of organic iodides is described. Catalytic Pd(OAc)2 with a stoichiometric amount of silver(I) trifluoroacetate enables the coupling process between either an (hetero)aryl or alkenyl iodide with ethenesulfonyl fluoride (ESF). The method is demonstrated in the successful syntheses of eighty-eight otherwise difficult to access compounds, in up to 99 % yields, including the unprecedented 2-heteroarylethenesulfonyl fluorides and 1,3-dienylsulfonyl fluorides.

Entities: CellLine Chemical Disease Gene

Keywords: alkenes; click chemistry; drug discovery; fluorine; palladium

Year: 2017 PMID： 28370917 PMCID： PMC5653204 DOI： 10.1002/anie.201701162

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

12 in total

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Authors: Praveen K Chinthakindi; Kimberleigh B Govender; A Sanjeeva Kumar; Hendrik G Kruger; Thavendran Govender; Tricia Naicker; Per I Arvidsson
Journal: Org Lett Date: 2017-01-11 Impact factor: 6.005

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4. Sulfur(VI) fluoride exchange (SuFEx): another good reaction for click chemistry.

Authors: Jiajia Dong; Larissa Krasnova; M G Finn; K Barry Sharpless
Journal: Angew Chem Int Ed Engl Date: 2014-08-11 Impact factor: 15.336

5. Ethenesulfonyl Fluoride (ESF): An On-Water Procedure for the Kilogram-Scale Preparation.

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Journal: J Org Chem Date: 2016-11-03 Impact factor: 4.354

6. Multidimensional SuFEx Click Chemistry: Sequential Sulfur(VI) Fluoride Exchange Connections of Diverse Modules Launched From An SOF₄ Hub.

Authors: Suhua Li; Peng Wu; John E Moses; K Barry Sharpless
Journal: Angew Chem Int Ed Engl Date: 2017-02-06 Impact factor: 15.336

7. A Heck-Matsuda Process for the Synthesis of β-Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry.

Authors: Hua-Li Qin; Qinheng Zheng; Grant A L Bare; Peng Wu; K Barry Sharpless
Journal: Angew Chem Int Ed Engl Date: 2016-10-10 Impact factor: 15.336

8. Arylfluorosulfates Inactivate Intracellular Lipid Binding Protein(s) through Chemoselective SuFEx Reaction with a Binding Site Tyr Residue.

Authors: Wentao Chen; Jiajia Dong; Lars Plate; David E Mortenson; Gabriel J Brighty; Suhua Li; Yu Liu; Andrea Galmozzi; Peter S Lee; Jonathan J Hulce; Benjamin F Cravatt; Enrique Saez; Evan T Powers; Ian A Wilson; K Barry Sharpless; Jeffery W Kelly
Journal: J Am Chem Soc Date: 2016-06-02 Impact factor: 15.419

9. SuFEx-based synthesis of polysulfates.

Authors: Jiajia Dong; Luke Kwisnek; James S Oakdale; K Barry Sharpless; Valery V Fokin
Journal: Angew Chem Int Ed Engl Date: 2014-08-05 Impact factor: 15.336

10. Proteasome inhibition by new dual warhead containing peptido vinyl sulfonyl fluorides.

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13 in total

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Authors: Bing Gao; Suhua Li; Peng Wu; John E Moses; K Barry Sharpless
Journal: Angew Chem Int Ed Engl Date: 2018-01-16 Impact factor: 15.336

2. SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase.

Authors: Qinheng Zheng; Jordan L Woehl; Seiya Kitamura; Diogo Santos-Martins; Christopher J Smedley; Gencheng Li; Stefano Forli; John E Moses; Dennis W Wolan; K Barry Sharpless
Journal: Proc Natl Acad Sci U S A Date: 2019-09-04 Impact factor: 11.205

3. Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF₄ )-Derived Connective Hubs for Bioconjugation to DNA and Proteins.

Authors: Feng Liu; Hua Wang; Suhua Li; Grant A L Bare; Xuemin Chen; Chu Wang; John E Moses; Peng Wu; K Barry Sharpless
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4. C(alkenyl)-H Activation via Six-Membered Palladacycles: Catalytic 1,3-Diene Synthesis.

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Journal: J Am Chem Soc Date: 2018-04-23 Impact factor: 15.419

5. Ethenesulfonyl fluoride derivatives as telomerase inhibitors: structure-based design, SAR, and anticancer evaluation in vitro.

Authors: Xing Chen; Gao-Feng Zha; Jie Quan Wang; Xin-Hua Liu
Journal: J Enzyme Inhib Med Chem Date: 2018-12 Impact factor: 5.051

6. Rh-Catalyzed Highly Enantioselective Synthesis of Aliphatic Sulfonyl Fluorides.

Authors: Balakrishna Moku; Wan-Yin Fang; Jing Leng; Linxian Li; Gao-Feng Zha; K P Rakesh; Hua-Li Qin
Journal: iScience Date: 2019-10-30

7. Cyclic Alkenylsulfonyl Fluorides: Palladium-Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents.

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Journal: Angew Chem Int Ed Engl Date: 2019-11-06 Impact factor: 15.336