Literature DB >> 25476241

Palladium-catalyzed intramolecular C-H difluoroalkylation: synthesis of substituted 3,3-difluoro-2-oxindoles.

Shi-Liang Shi1, Stephen L Buchwald.   

Abstract

The synthesis of 3,3-difluoro-2-oxindoles through a robust and efficient palladium-catalyzed CH difluoroalkylation is described. This process generates a broad range of difluorooxindoles from readily prepared starting materials. The use of BrettPhos as the ligand was crucial for high efficiency. Preliminary mechanistic studies suggest that oxidative addition is the rate-determining step for this process.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; cross-coupling; fluorine; heterocycles; palladium

Mesh：

Substances：

Year:  2014        PMID： 25476241      PMCID： PMC4384468          DOI： 10.1002/anie.201410471

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


  57 in total

1.  A new method for aromatic difluoromethylation: copper-catalyzed cross-coupling and decarboxylation sequence from aryl iodides.

Authors:  Kenichi Fujikawa; Yasutaka Fujioka; Akira Kobayashi; Hideki Amii
Journal:  Org Lett       Date:  2011-09-28       Impact factor: 6.005

2.  Facile Ar-CF3 bond formation at Pd. Strikingly different outcomes of reductive elimination from [(Ph3P)2Pd(CF3)Ph] and [(Xantphos)Pd(CF3)Ph].

Authors:  Vladimir V Grushin; William J Marshall
Journal:  J Am Chem Soc       Date:  2006-10-04       Impact factor: 15.419

3.  Discovery and SAR of oxindole-pyridine-based protein kinase B/Akt inhibitors for treating cancers.

Authors:  Gui-Dong Zhu; Viraj B Gandhi; Jianchun Gong; Yan Luo; Xuesong Liu; Yan Shi; Ran Guan; Shayna R Magnone; Vered Klinghofer; Eric F Johnson; Jennifer Bouska; Alexander Shoemaker; Anatol Oleksijew; Ken Jarvis; Chang Park; Ron De Jong; Tilman Oltersdorf; Qun Li; Saul H Rosenberg; Vincent L Giranda
Journal:  Bioorg Med Chem Lett       Date:  2006-04-27       Impact factor: 2.823

4.  The palladium-catalyzed trifluoromethylation of vinyl sulfonates.

Authors:  Eun Jin Cho; Stephen L Buchwald
Journal:  Org Lett       Date:  2011-11-23       Impact factor: 6.005

5.  Unexpected H2O-induced Ar-X activation with trifluoromethylpalladium(II) aryls.

Authors:  Vladimir V Grushin; William J Marshall
Journal:  J Am Chem Soc       Date:  2006-04-12       Impact factor: 15.419

Review 6.  Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors:  Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal:  Chem Rev       Date:  2013-12-03       Impact factor: 60.622

7.  Copper-mediated difluoromethylation of (hetero)aryl iodides and β-styryl halides with tributyl(difluoromethyl)stannane.

Authors:  G K Surya Prakash; Somesh K Ganesh; John-Paul Jones; Aditya Kulkarni; Kamil Masood; Joseph K Swabeck; George A Olah
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-25       Impact factor: 15.336

8.  Direct synthesis of fluorinated heteroarylether bioisosteres.

Authors:  Qianghui Zhou; Alessandro Ruffoni; Ryan Gianatassio; Yuta Fujiwara; Eran Sella; Doron Shabat; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-04       Impact factor: 15.336

9.  Pd-catalyzed α-arylation of trimethylsilyl enolates of α,α-difluoroacetamides.

Authors:  Shaozhong Ge; Sophie I Arlow; Michael G Mormino; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-10-03       Impact factor: 15.419

10.  Pd-catalyzed nucleophilic fluorination of aryl bromides.

Authors:  Hong Geun Lee; Phillip J Milner; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2014-02-27       Impact factor: 15.419
View more
  5 in total

Review 1.  The Fascinating Chemistry of α-Haloamides.

Authors:  Anna Fantinati; Vinicio Zanirato; Paolo Marchetti; Claudio Trapella
Journal:  ChemistryOpen       Date:  2020-01-13       Impact factor: 2.911

2.  Optimized Synthesis of a Pentafluoro-gem-diol and Conversion to a CF2Br-Glucopyranose through Trifluoroacetate-Release and Halogenation.

Authors:  Robert A Hazlitt; Jinu P John; Que-Lynn Tran; David A Colby
Journal:  Tetrahedron Lett       Date:  2016-03-19       Impact factor: 2.415

3.  Copper-Catalyzed Cyclopropanol Ring Opening Csp(3)-Csp(3) Cross-Couplings with (Fluoro)Alkyl Halides.

Authors:  Zhishi Ye; Kristen E Gettys; Xingyu Shen; Mingji Dai
Journal:  Org Lett       Date:  2015-12-04       Impact factor: 6.005

4.  Catalytic asymmetric radical aminoperfluoroalkylation and aminodifluoromethylation of alkenes to versatile enantioenriched-fluoroalkyl amines.

Authors:  Jin-Shun Lin; Fu-Li Wang; Xiao-Yang Dong; Wei-Wei He; Yue Yuan; Su Chen; Xin-Yuan Liu
Journal:  Nat Commun       Date:  2017-03-23       Impact factor: 14.919

5.  Difluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel.

Authors:  Chang Xu; Wen-Hao Guo; Xu He; Yin-Long Guo; Xue-Ying Zhang; Xingang Zhang
Journal:  Nat Commun       Date:  2018-03-21       Impact factor: 14.919
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.