Literature DB >> 25236851

BrettPhos ligand supported palladium-catalyzed C-O bond formation through an electronic pathway of reductive elimination: fluoroalkoxylation of activated aryl halides.

T M Rangarajan1, Rajendra Singh, Raju Brahma, Kavita Devi, Rishi Pal Singh, R P Singh, Ashok K Prasad.   

Abstract

We report an unprecedented BrettPhos ligand supported Pd-catalyzed CO bond-forming reaction of activated aryl halides with primary fluoroalkyl alcohols. We demonstrate that the Phosphine ligand (BrettPhos) possesses the property of altering the mechanistic pathway of reductive elimination from nucleophile to nucleophile. The Pd/BrettPhos catalyst system facilitates the reductive elimination of the oxygen nucleophile through an electronic pathway.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  BrettPhos; CO coupling; alcohols; ethers; reductive elimination

Year:  2014        PMID: 25236851     DOI: 10.1002/chem.201404121

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  8 in total

1.  Improved Process for the Palladium-Catalyzed C-O Cross-Coupling of Secondary Alcohols.

Authors:  Hong Zhang; Paula Ruiz-Castillo; Alexander W Schuppe; Stephen L Buchwald
Journal:  Org Lett       Date:  2020-06-24       Impact factor: 6.005

2.  Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides.

Authors:  Christian A Malapit; Naoko Ichiishi; Melanie S Sanford
Journal:  Org Lett       Date:  2017-07-19       Impact factor: 6.005

3.  Palladium-Catalyzed C-O Cross-Coupling of Primary Alcohols.

Authors:  Hong Zhang; Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Org Lett       Date:  2018-02-23       Impact factor: 6.005

4.  Oxalohydrazide Ligands for Copper-Catalyzed C-O Coupling Reactions with High Turnover Numbers.

Authors:  Ritwika Ray; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-03       Impact factor: 15.336

5.  Visible-light-induced aerobic C3-H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols.

Authors:  Xiaobo Xu; Chengcai Xia; Xiaojun Li; Jian Sun; Liqiang Hao
Journal:  RSC Adv       Date:  2020-01-09       Impact factor: 4.036

6.  Chemoselective, Scalable Nickel-Electrocatalytic O-Arylation of Alcohols.

Authors:  Hai-Jun Zhang; Longrui Chen; Martins S Oderinde; Jacob T Edwards; Yu Kawamata; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-15       Impact factor: 16.823

7.  Synthesis and Evaluation of Antiplasmodial Activity of 2,2,2-Trifluoroethoxychalcones and 2-Fluoroethoxy Chalcones against Plasmodium falciparum in Culture.

Authors:  Kavita Devi; Vinoth Rajendran; T M Rangarajan; Rishi Pal Singh; Prahlad C Ghosh; Manjula Singh
Journal:  Molecules       Date:  2018-05-14       Impact factor: 4.411

8.  Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C-O Cross-Coupling.

Authors:  Robert Szpera; Patrick G Isenegger; Maxime Ghosez; Natan J W Straathof; Rosa Cookson; David C Blakemore; Paul Richardson; Véronique Gouverneur
Journal:  Org Lett       Date:  2020-08-04       Impact factor: 6.005

  8 in total

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