Literature DB >> 20825168

Iron-catalyzed heterocycle and arene deprotonative alkylation.

Ly Dieu Tran1, Olafs Daugulis.   

Abstract

A method for iron-catalyzed deprotonative alkylation of arene C-H bonds by alkyl iodides and bromides has been developed. In the presence of an amide base, both primary and secondary alkyl halides can be coupled with furans, thiophenes, pyridine derivatives, and some electron-withdrawing-group containing arenes.

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Year:  2010        PMID： 20825168      PMCID： PMC2952416          DOI： 10.1021/ol101684u

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  38 in total

1.  Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

2.  A reassessment of the transition-metal free suzuki-type coupling methodology.

Authors:  Riina K Arvela; Nicholas E Leadbeater; Michael S Sangi; Victoria A Williams; Patricia Granados; Robert D Singer
Journal:  J Org Chem       Date:  2005-01-07       Impact factor: 4.354

3.  Mixed Mg/Li amides of the type R2NMgCl.LiCl as highly efficient bases for the regioselective generation of functionalized aryl and heteroaryl magnesium compounds.

Authors:  Arkady Krasovskiy; Valeria Krasovskaya; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2006-04-28       Impact factor: 15.336

Review 4.  Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Authors:  Dino Alberico; Mark E Scott; Mark Lautens
Journal:  Chem Rev       Date:  2007-01       Impact factor: 60.622

5.  Iron-catalyzed alkylations of aromatic grignard reagents.

Authors:  Gérard Cahiez; Vanessa Habiak; Christophe Duplais; Alban Moyeux
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  The nickel/copper-catalyzed direct alkylation of heterocyclic C-H bonds.

Authors:  Oleg Vechorkin; Valérie Proust; Xile Hu
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-12       Impact factor: 15.336

7.  Palladium(II)-catalyzed ortho alkylation of benzoic acids with alkyl halides.

Authors:  Yang-Hui Zhang; Bing-Feng Shi; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Preparation of functionalized aryl iron(II) compounds and a nickel-catalyzed cross-coupling with alkyl halides.

Authors:  Stefan H Wunderlich; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Application of Daugulis copper-catalyzed direct arylation to the synthesis of 5-aryl benzotriazepines.

Authors:  Sirilata Yotphan; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

Review 10.  Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Authors:  Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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  7 in total

1.  Rh(I)-catalyzed direct arylation of azines.

Authors:  Ashley M Berman; Robert G Bergman; Jonathan A Ellman
Journal:  J Org Chem       Date:  2010-10-29       Impact factor: 4.354

2.  C-H and C-N Activation at Redox-Active Pyridine Complexes of Iron.

Authors:  K Cory MacLeod; Richard A Lewis; Daniel E DeRosha; Brandon Q Mercado; Patrick L Holland
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-21       Impact factor: 15.336

3.  Synthesis of Diarylated 4-Pyridylmethyl Ethers via Palladium-Catalyzed Cross-Coupling Reactions.

Authors:  Keyume Ablajan; Grace B Panetti; Xiaodong Yang; Byeong-Seon Kim; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2017-05-23       Impact factor: 5.837

4.  Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

Authors:  Enrico T Nadres; Gerson Ivan Franco Santos; Dmitry Shabashov; Olafs Daugulis
Journal:  J Org Chem       Date:  2013-09-19       Impact factor: 4.354

5.  Iron-catalyzed arylation of heterocycles via directed C-H bond activation.

Authors:  John J Sirois; Riley Davis; Brenton DeBoef
Journal:  Org Lett       Date:  2014-01-22       Impact factor: 6.005

6.  The theoretical chemical calculations clarify the mechanism of beta-alkylation of 1-phenylethanol with benzyl alcohol catalyzed by iron(ii) acetylacetonate methods.

Authors:  Wei Feng; Junfeng Zhao; Aiwen Wei; Dandan Zhang; Huiling Liu; Xuri Huang; Kai Sun
Journal:  RSC Adv       Date:  2018-07-03       Impact factor: 3.361

7.  Nickel-Catalyzed Arylation of Heteroaryl-containing Diarylmethanes: Exceptional Reactivity of the Ni(NIXANTPHOS)-based Catalyst.

Authors:  Xinyu Cao; Sheng-Chun Sha; Minyan Li; Byeong-Seon Kim; Catherine Morgan; Rudan Huang; Xiaodong Yang; Patrick J Walsh
Journal:  Chem Sci       Date:  2015-10-26       Impact factor: 9.825
  7 in total

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