Literature DB >> 24955892

Iron-catalyzed borylation of alkyl electrophiles.

Thomas C Atack1, Rachel M Lecker, Silas P Cook.   

Abstract

The use of low-cost iron(III) acetoacetate (Fe(acac)3) and tetramethylethylenediamine (TMEDA) enables the direct cross-coupling of alkyl halides with bis(pinacolato)diboron. This approach allows for the borylation of activated or unactivated primary, secondary, and tertiary bromides. Moreover, even the borylation of benzylic or allylic chlorides, tosylates, and mesylates are possible. The reactions proceed under mild conditions at room temperature and show broad functional-group compatibility and "robustness" as measured by a modified Glorius robustness screen.

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Year:  2014        PMID: 24955892     DOI: 10.1021/ja505199u

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  24 in total

1.  Decarboxylative borylation.

Authors:  Chao Li; Jie Wang; Lisa M Barton; Shan Yu; Maoqun Tian; David S Peters; Manoj Kumar; Antony W Yu; Kristen A Johnson; Arnab K Chatterjee; Ming Yan; Phil S Baran
Journal:  Science       Date:  2017-04-13       Impact factor: 47.728

2.  Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.

Authors:  Michael R Hollerbach; Timothy J Barker
Journal:  Organometallics       Date:  2018-04-27       Impact factor: 3.876

3.  Practical, efficient, and broadly applicable synthesis of readily differentiable vicinal diboronate compounds by catalytic three-component reactions.

Authors:  Suttipol Radomkit; Zhenxing Liu; Anna Closs; Malte S Mikus; Amir H Hoveyda
Journal:  Tetrahedron       Date:  2017-05-20       Impact factor: 2.457

4.  Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes.

Authors:  Amberly B Sanford; Taylor A Thane; Tristan M McGinnis; Pan-Pan Chen; Xin Hong; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2020-03-04       Impact factor: 15.419

5.  Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.

Authors:  Hilary A Kerchner; John Montgomery
Journal:  Org Lett       Date:  2016-10-27       Impact factor: 6.005

6.  Electrochemical borylation of carboxylic acids.

Authors:  Lisa M Barton; Longrui Chen; Donna G Blackmond; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2021-08-24       Impact factor: 11.205

7.  Additive and Counterion Effects in Iron-Catalyzed Reactions Relevant to C-C Bond Formation.

Authors:  Nikki J Bakas; Michael L Neidig
Journal:  ACS Catal       Date:  2021-06-29       Impact factor: 13.700

8.  Catalytic Carbo- and Aminoboration of Alkenyl Carbonyl Compounds via Five- and Six-Membered Palladacycles.

Authors:  Zhen Liu; Hui-Qi Ni; Tian Zeng; Keary M Engle
Journal:  J Am Chem Soc       Date:  2018-02-07       Impact factor: 15.419

9.  Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters.

Authors:  Spencer O Scholz; Jesse B Kidd; Luca Capaldo; Niecia E Flikweert; Rowan M Littlefield; Tehshik P Yoon
Journal:  Org Lett       Date:  2021-04-12       Impact factor: 6.005

10.  Highly Diastereoselective Construction of Carbon- Heteroatom Quaternary Stereogenic Centers in the Synthesis of Analogs of Bioactive Compounds: From Monofluorinated Epoxyalkylphosphonates to α-Fluoro-, β-, or γ-Amino Alcohol Derivatives of Alkylphosphonates.

Authors:  Magdalena Rapp; Klaudia Margas-Musielak; Patrycja Kaczmarek; Agnieszka Witkowska; Tomasz Cytlak; Tomasz Siodła; Henryk Koroniak
Journal:  Front Chem       Date:  2021-06-02       Impact factor: 5.221

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