Literature DB >> 17274623

One-pot synthesis of arylboronic acids and aryl trifluoroborates by Ir-catalyzed borylation of arenes.

Jaclyn M Murphy1, C Christoph Tzschucke, John F Hartwig.   

Abstract

[reaction: see text] The synthesis of arylboronic acids and aryl trifluoroborates in a one-pot sequence by Ir-catalyzed borylation of arenes is reported. To prepare the arylboronic acids, the Ir-catalyzed borylation is followed by oxidative cleavage of the boronic ester with NaIO4. To prepare the aryltrifluoroborate, the Ir-catalyzed borylation is followed by displacement of pinacol by KHF2. These two-step sequences give products that are more reactive toward subsequent chemistry than the initially formed pinacol boronates.

Entities:  

Year:  2007        PMID: 17274623     DOI: 10.1021/ol062903o

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


  16 in total

1.  Cationic tricoordinate boron intermediates: borenium chemistry from the organic perspective.

Authors:  Timothy S De Vries; Aleksandrs Prokofjevs; Edwin Vedejs
Journal:  Chem Rev       Date:  2012-04-20       Impact factor: 60.622

2.  PyDipSi: a general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes.

Authors:  Natalia Chernyak; Alexander S Dudnik; Chunhui Huang; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

3.  Catalyst-Controlled Site-Selective Bond Activation.

Authors:  John F Hartwig
Journal:  Acc Chem Res       Date:  2017-03-21       Impact factor: 22.384

4.  Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: a simplified route to diverse boronate ester derivatives.

Authors:  Gary A Molander; Sarah L J Trice; Spencer D Dreher
Journal:  J Am Chem Soc       Date:  2010-11-24       Impact factor: 15.419

5.  Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid.

Authors:  Gary A Molander; Sarah L J Trice; Steven M Kennedy; Spencer D Dreher; Matthew T Tudge
Journal:  J Am Chem Soc       Date:  2012-07-06       Impact factor: 15.419

6.  Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2012-04-24       Impact factor: 4.354

7.  Iterative Cross-Couplng with MIDA Boronates: Towards a General Platform for Small Molecule Synthesis.

Authors:  Eric P Gillis; Martin D Burke
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

8.  Meta-selective C-H functionalization using a nitrile-based directing group and cleavable Si-tether.

Authors:  Sunggi Lee; Hyelee Lee; Kian L Tan
Journal:  J Am Chem Soc       Date:  2013-12-10       Impact factor: 15.419

9.  The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes.

Authors:  Chunhui Huang; Natalia Chernyak; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Adv Synth Catal       Date:  2011-05-01       Impact factor: 5.837

10.  Superelectrophilic intermediates in nitrogen-directed aromatic borylation.

Authors:  Timothy S De Vries; Aleksandrs Prokofjevs; Jeremy N Harvey; Edwin Vedejs
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

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