Literature DB >> 24505002

Site-differentiated polyboron arenes prepared by direct C-H borylation and their highly selective Suzuki-Miyaura cross-coupling reactions.

Liang Xu1, Siyi Ding, Pengfei Li.   

Abstract

Di- and polyboron (hetero)arenes, site-differentiated with MIDA boronyl (MIDA=N-methyliminodiacetic acid) and pinacolato boronyl (Bpin), were prepared by an iridium-catalyzed direct CH borylation of readily available (hetero)aryl MIDA boronates. The excellent synthetic uses of these multisite nucleophiles were demonstrated by the high-yield production of a variety of multifunctionalized poly(hetero)arenes with the highly chemoselective Suzuki-Miyaura coupling (SMC) of the Bpin moiety being an essential step.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH functionalization; boron; chemoselectivity; homogeneous catalysis; synthetic methods

Year:  2014        PMID： 24505002     DOI： 10.1002/anie.201309546

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


  9 in total

1.  Enantioselective Borylation of Aromatic C-H Bonds with Chiral Dinitrogen Ligands.

Authors:  Bo Su; Tai-Gang Zhou; Pei-Lin Xu; Zhang-Jie Shi; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-16       Impact factor: 15.336

2.  Regiocontrolled allylic functionalization of internal alkene via selenium-π-acid catalysis guided by boron substitution.

Authors:  Ling Yang; Yuan Liu; Wen-Xin Fan; Dong-Hang Tan; Qingjiang Li; Honggen Wang
Journal:  Chem Sci       Date:  2022-04-22       Impact factor: 9.969

3.  Chemoselective boronic ester synthesis by controlled speciation.

Authors:  James W B Fyfe; Ciaran P Seath; Allan J B Watson
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-29       Impact factor: 15.336

4.  Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C-H Activation and Orthogonal Reactivity.

Authors:  Emilien Demory; Karthik Devaraj; Andreas Orthaber; Paul J Gates; Lukasz T Pilarski
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-13       Impact factor: 15.336

5.  Chemoselective oxidation of aryl organoboron systems enabled by boronic acid-selective phase transfer.

Authors:  John J Molloy; Thomas A Clohessy; Craig Irving; Niall A Anderson; Guy C Lloyd-Jones; Allan J B Watson
Journal:  Chem Sci       Date:  2016-10-27       Impact factor: 9.825

6.  Catalyst shuttling enabled by a thermoresponsive polymeric ligand: facilitating efficient cross-couplings with continuously recyclable ppm levels of palladium.

Authors:  Erfei Wang; Mao Chen
Journal:  Chem Sci       Date:  2019-07-23       Impact factor: 9.825

7.  Use of N-methyliminodiacetic acid boronate esters in suzuki-miyaura cross-coupling polymerizations of triarylamine and fluorene monomers.

Authors:  Andrew B Foster; Viktor Bagutski; Josue I Ayuso-Carrillo; Martin J Humphries; Michael J Ingleson; Michael L Turner
Journal:  J Polym Sci A Polym Chem       Date:  2017-07-03       Impact factor: 2.702

8.  Mild and Efficient Synthesis of Diverse Organo-AuI -L Complexes in Green Solvents.

Authors:  Fredric J L Ingner; Ann-Cathrin Schmitt; Andreas Orthaber; Paul J Gates; Lukasz T Pilarski
Journal:  ChemSusChem       Date:  2020-03-03       Impact factor: 8.928

9.  Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions.

Authors:  Kai Chen; Shuai Zhang; Pei He; Pengfei Li
Journal:  Chem Sci       Date:  2016-02-01       Impact factor: 9.825
  9 in total

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