Literature DB >> 26136406

Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process.

Martin Pichette Drapeau1,2, Indira Fabre3,4, Laurence Grimaud3, Ilaria Ciofini4, Thierry Ollevier2, Marc Taillefer5.   

Abstract

The α-arylation of enolizable aryl ketones can be carried out with aryl halides under transition-metal-free conditions using KOtBu in DMF. The α-aryl ketones thus obtained can be used for step- and cost-economic syntheses of fused heterocycles and Tamoxifen. Mechanistic studies demonstrate the synergetic role of base and solvent for the initiation of the radical process.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CC coupling; arylation; ketones; reaction mechanisms

Year:  2015        PMID： 26136406     DOI： 10.1002/anie.201502332

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


  15 in total

1.  Mechanistic insights into the potassium tert-butoxide-mediated synthesis of N-heterobiaryls.

Authors:  David E Stephens; Johant Lakey-Beitia; Jessica E Burch; Hadi D Arman; Oleg V Larionov
Journal:  Chem Commun (Camb)       Date:  2016-08-02       Impact factor: 6.222

2.  Critical Assessment of the Reducing Ability of Breslow-type Derivatives and Implications for Carbene-Catalyzed Radical Reactions*.

Authors:  Ludivine Delfau; Samantha Nichilo; Florian Molton; Julie Broggi; Eder Tomás-Mendivil; David Martin
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-15       Impact factor: 16.823

3.  Ligand-Mediated and Copper-Catalyzed C(sp(3))-H Bond Functionalization of Aryl Ketones with Sodium Sulfinates under Mild Conditions.

Authors:  Xing-Wang Lan; Nai-Xing Wang; Cui-Bing Bai; Wei Zhang; Yalan Xing; Jia-Long Wen; Yan-Jing Wang; Yi-He Li
Journal:  Sci Rep       Date:  2015-12-18       Impact factor: 4.379

4.  Direct arylation catalysis with chloro[8-(dimesitylboryl)quinoline-κN]copper(I).

Authors:  Sem Raj Tamang; James D Hoefelmeyer
Journal:  Beilstein J Org Chem       Date:  2016-12-15       Impact factor: 2.883

5.  Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and β-ketoamides.

Authors:  Irwan Iskandar Roslan; Kian-Hong Ng; Gaik-Khuan Chuah; Stephan Jaenicke
Journal:  Beilstein J Org Chem       Date:  2017-12-18       Impact factor: 2.883

6.  Divergent Synthetic Access to E- and Z-Stereodefined All-Carbon-Substituted Olefin Scaffolds: Application to Parallel Synthesis of (E)- and (Z)-Tamoxifens.

Authors:  Yuichiro Ashida; Atsushi Honda; Yuka Sato; Hidefumi Nakatsuji; Yoo Tanabe
Journal:  ChemistryOpen       Date:  2017-01-18       Impact factor: 2.911

7.  KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones.

Authors:  Qiao Lin; Shiling Zhang; Bin Li
Journal:  Beilstein J Org Chem       Date:  2020-03-25       Impact factor: 2.883

8.  Electrochemical oxidative decarboxylation and 1,2-aryl migration towards the synthesis of 1,2-diaryl ethers.

Authors:  Faxiang Bu; Lijun Lu; Xia Hu; Shengchun Wang; Heng Zhang; Aiwen Lei
Journal:  Chem Sci       Date:  2020-09-02       Impact factor: 9.825

9.  Testing the limits of radical-anionic CH-amination: a 10-million-fold decrease in basicity opens a new path to hydroxyisoindolines via a mixed C-N/C-O-forming cascade.

Authors:  Quintin Elliott; Gabriel Dos Passos Gomes; Christopher J Evoniuk; Igor V Alabugin
Journal:  Chem Sci       Date:  2020-02-21       Impact factor: 9.825

10.  Enantioselective Oxidative Rearrangements with Chiral Hypervalent Iodine Reagents.

Authors:  Michael Brown; Ravi Kumar; Julia Rehbein; Thomas Wirth
Journal:  Chemistry       Date:  2016-01-21       Impact factor: 5.236
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