Literature DB >> 32697365

Copper-Catalyzed Oxidative Cross-Coupling of Electron-Deficient Polyfluorophenylboronate Esters with Terminal Alkynes.

Zhiqiang Liu1, Yudha P Budiman1,2, Ya-Ming Tian1, Alexandra Friedrich1, Mingming Huang1, Stephen A Westcott3, Udo Radius1, Todd B Marder1.   

Abstract

We report herein a mild procedure for the copper-catalyzed oxidative cross-coupling of electron-deficient <span class="Chemical">polyfluorophenylboronate esters with terminal alkynes. This method displays good functional group tolerance and broad substrate scope, generating cross-coupled alkynyl(fluoro)arene products in moderate to excellent yields. Thus, it represents a simple alternative to the conventional Sonogashira reaction.
© 2020 The Authors. Published by Wiley-VCH GmbH.

Entities:  

Keywords:  Sonogashira reaction; boronate esters; coupling reactions; fluorine; fluoroarenes

Year:  2020        PMID： 32697365      PMCID： PMC7821263          DOI： 10.1002/chem.202002888

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


  73 in total

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3.  Selectivity of C-H Activation and Competition between C-H and C-F Bond Activation at Fluorocarbons.

Authors:  Odile Eisenstein; Jessica Milani; Robin N Perutz
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4.  Synthesis of fluorinated building blocks by transition-metal-mediated hydrodefluorination reactions.

Authors:  Moritz F Kuehnel; Dieter Lentz; Thomas Braun
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5.  Copper/silver-mediated direct ortho-ethynylation of unactivated (hetero)aryl C-H bonds with terminal alkyne.

Authors:  Yue-Jin Liu; Yan-Hua Liu; Xue-Song Yin; Wen-Jia Gu; Bing-Feng Shi
Journal:  Chemistry       Date:  2014-11-14       Impact factor: 5.236

6.  GaCl(3)-catalyzed ortho-ethynylation of phenols.

Authors:  Katsumi Kobayashi; Mieko Arisawa; Masahiko Yamaguchi
Journal:  J Am Chem Soc       Date:  2002-07-24       Impact factor: 15.419

7.  Preparation of conjugated 1,3-enynes by Rh(III)-catalysed alkynylation of alkenes via C-H activation.

Authors:  Karl D Collins; Fabian Lied; Frank Glorius
Journal:  Chem Commun (Camb)       Date:  2014-03-20       Impact factor: 6.222

8.  Structure and phase behavior of a 2:1 complex between arene- and fluoroarene-based conjugated rigid rods.

Authors:  Stephen W Watt; Chaoyang Dai; Andrew J Scott; Jacquelyn M Burke; Rhodri Ll Thomas; Jonathan C Collings; Christopher Viney; William Clegg; Todd B Marder
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-07       Impact factor: 15.336

9.  Rh(III)- and Ir(III)-catalyzed C-H alkynylation of arenes under chelation assistance.

Authors:  Fang Xie; Zisong Qi; Songjie Yu; Xingwei Li
Journal:  J Am Chem Soc       Date:  2014-03-14       Impact factor: 15.419

10.  Stereodefined trisubstituted enolates as a unique entry to all-carbon quaternary stereogenic centers in acyclic systems.

Authors:  Yury Minko; Morgane Pasco; Lukas Lercher; Ilan Marek
Journal:  Nat Protoc       Date:  2013-03-21       Impact factor: 13.491
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  2 in total

1.  Coligand role in the NHC nickel catalyzed C-F bond activation: investigations on the insertion of bis(NHC) nickel into the C-F bond of hexafluorobenzene.

Authors:  Maximilian W Kuntze-Fechner; Hendrik Verplancke; Lukas Tendera; Martin Diefenbach; Ivo Krummenacher; Holger Braunschweig; Todd B Marder; Max C Holthausen; Udo Radius
Journal:  Chem Sci       Date:  2020-10-06       Impact factor: 9.825

2.  Copper-Catalyzed Oxidative Cross-Coupling of Electron-Deficient Polyfluorophenylboronate Esters with Terminal Alkynes.

Authors:  Zhiqiang Liu; Yudha P Budiman; Ya-Ming Tian; Alexandra Friedrich; Mingming Huang; Stephen A Westcott; Udo Radius; Todd B Marder
Journal:  Chemistry       Date:  2020-11-09       Impact factor: 5.236
  2 in total

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