Literature DB >> 25350556

Silver-catalyzed radical fluorination of alkylboronates in aqueous solution.

Zhaodong Li1, Zhentao Wang, Lin Zhu, Xinqiang Tan, Chaozhong Li.   

Abstract

We report herein an efficient and general method for the deboronofluorination of alkylboronates. Thus, with the catalysis of AgNO3, the reactions of various alkylboronic acids or their pinacol esters with Selectfluor reagent in acidic aqueous solution afforded the corresponding alkyl fluorides under mild conditions. A broad substrate scope and wide functional group compatibility were observed. A radical mechanism is proposed for this site-specific fluorination.

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Year:  2014        PMID： 25350556     DOI： 10.1021/ja509548z

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  16 in total

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Authors:  Zhen Liu; Jiahao Chen; Hou-Xiang Lu; Xiaohan Li; Yang Gao; John R Coombs; Matthew J Goldfogel; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-08       Impact factor: 15.336

2.  Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.

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Journal:  Angew Chem Int Ed Engl       Date:  2019-11-07       Impact factor: 15.336

3.  Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents.

Authors:  Xinghua Ma; Mohamed Diane; Glenn Ralph; Christine Chen; Mark R Biscoe
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-04       Impact factor: 15.336

4.  Hydroxy-directed fluorination of remote unactivated C(sp3)-H bonds: a new age of diastereoselective radical fluorination.

Authors:  Stefan Andrew Harry; Michael Richard Xiang; Eric Holt; Andrea Zhu; Fereshte Ghorbani; Dhaval Patel; Thomas Lectka
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

5.  Ligand-Promoted Borylation of C(sp(3))-H Bonds with Palladium(II) Catalysts.

Authors:  Jian He; Heng Jiang; Ryosuke Takise; Ru-Yi Zhu; Gang Chen; Hui-Xiong Dai; T G Murali Dhar; Jun Shi; Hao Zhang; Peter T W Cheng; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-27       Impact factor: 15.336

6.  Catalytic Carbo- and Aminoboration of Alkenyl Carbonyl Compounds via Five- and Six-Membered Palladacycles.

Authors:  Zhen Liu; Hui-Qi Ni; Tian Zeng; Keary M Engle
Journal:  J Am Chem Soc       Date:  2018-02-07       Impact factor: 15.419

7.  Aqueous Benzylic C-H Trifluoromethylation for Late-Stage Functionalization.

Authors:  Shuo Guo; Deyaa I AbuSalim; Silas P Cook
Journal:  J Am Chem Soc       Date:  2018-09-24       Impact factor: 15.419

8.  Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters.

Authors:  Spencer O Scholz; Jesse B Kidd; Luca Capaldo; Niecia E Flikweert; Rowan M Littlefield; Tehshik P Yoon
Journal:  Org Lett       Date:  2021-04-12       Impact factor: 6.005

9.  Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cations.

Authors:  Cody Ross Pitts; Michelle Sheanne Bloom; Desta Doro Bume; Qinze Arthur Zhang; Thomas Lectka
Journal:  Chem Sci       Date:  2015-06-23       Impact factor: 9.825

10.  Selective uni- and bidirectional homologation of diborylmethane.

Authors:  Daniel J Blair; Damiano Tanini; Joseph M Bateman; Helen K Scott; Eddie L Myers; Varinder K Aggarwal
Journal:  Chem Sci       Date:  2017-02-09       Impact factor: 9.825
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