Literature DB >> 30600852

Copper-Photocatalyzed Borylation of Organic Halides under Batch and Continuous-Flow Conditions.

Antoine Nitelet1, Damien Thevenet2, Bruno Schiavi2, Christophe Hardouin2, Jean Fournier2, Rodolphe Tamion2, Xavier Pannecoucke1, Philippe Jubault1, Thomas Poisson1,3.   

Abstract

The copper-photocatalyzed borylation of aryl, heteroaryl, vinyl and alkyl halides (I and Br) was reported. The reaction proceeded using a new heteroleptic Cu complex under irradiation with blue LEDs, giving the corresponding boronic-acid esters in good to excellent yields. The reaction was extended to continuous-flow conditions to allow an easy scale-up. The mechanism of the reaction was studied and a mechanism based on a reductive quenching (CuI /CuI */Cu0 ) was suggested.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  borylation; continuous flow; copper; photocatalysis; visible light

Year:  2019        PMID: 30600852     DOI: 10.1002/chem.201806345

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


  8 in total

Review 1.  Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

Authors:  Laura Buglioni; Fabian Raymenants; Aidan Slattery; Stefan D A Zondag; Timothy Noël
Journal:  Chem Rev       Date:  2021-08-10       Impact factor: 60.622

Review 2.  Inorganometallics (Transition Metal-Metalloid Complexes) and Catalysis.

Authors:  Bogdan Marciniec; Cezary Pietraszuk; Piotr Pawluć; Hieronim Maciejewski
Journal:  Chem Rev       Date:  2021-12-30       Impact factor: 60.622

3.  Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions.

Authors:  Daohong Yu; Wai-Pong To; Glenna So Ming Tong; Liang-Liang Wu; Kaai-Tung Chan; Lili Du; David Lee Phillips; Yungen Liu; Chi-Ming Che
Journal:  Chem Sci       Date:  2020-05-25       Impact factor: 9.825

Review 4.  Indolylboronic Acids: Preparation and Applications.

Authors:  Marek Čubiňák; Tereza Edlová; Peter Polák; Tomáš Tobrman
Journal:  Molecules       Date:  2019-09-28       Impact factor: 4.411

Review 5.  Recent advances in photocatalyzed reactions using well-defined copper(I) complexes.

Authors:  Mingbing Zhong; Xavier Pannecoucke; Philippe Jubault; Thomas Poisson
Journal:  Beilstein J Org Chem       Date:  2020-03-23       Impact factor: 2.883

Review 6.  New avenues for C-B bond formation via radical intermediates.

Authors:  Florian W Friese; Armido Studer
Journal:  Chem Sci       Date:  2019-09-03       Impact factor: 9.825

7.  Deoxygenative Borylation of Secondary and Tertiary Alcohols.

Authors:  Florian W Friese; Armido Studer
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-05       Impact factor: 15.336

8.  Aerobic Visible-Light-Driven Borylation of Heteroarenes in a Gel Nanoreactor.

Authors:  Jorge C Herrera-Luna; David Díaz Díaz; Alex Abramov; Susana Encinas; M Consuelo Jiménez; Raúl Pérez-Ruiz
Journal:  Org Lett       Date:  2021-03-02       Impact factor: 6.005

  8 in total

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