Literature DB >> 24347788

Electrophilic C-H Borylation and Related Reactions of B-H Boron Cations.

Aleksandrs Prokofjevs1, Janis Jermaks1, Alina Borovika1, Jeff W Kampf1, Edwin Vedejs1.   

Abstract

Catalytic procedures are described for aminedirected borylation of aliphatic and aromatic tertiary amine boranes. Sequential double borylation is observed in cases where two or more C-H bonds are available that allow 5-center or 6-center intramolecular borylation. The HNTf2 catalyzed borylation of benzylamine boranes provides a practical means for the synthesis of ortho-substituted arylboronic acid derivatives, suitable for Suzuki-Miyaura cross-coupling applications.

Entities:  

Year:  2013        PMID： 24347788      PMCID： PMC3857329          DOI： 10.1021/om400651p

Source DB:  PubMed          Journal:  Organometallics        ISSN： 0276-7333            Impact factor:   3.876


  16 in total

1.  Simple inexpensive boron electrophiles for direct arene borylation.

Authors:  Alessandro Del Grosso; Matthew D Helm; Sophia A Solomon; Dolores Caras-Quintero; Michael J Ingleson
Journal:  Chem Commun (Camb)       Date:  2011-10-21       Impact factor: 6.222

2.  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

Review 3.  Borinium, borenium, and boronium ions: synthesis, reactivity, and applications.

Authors:  Warren E Piers; Sara C Bourke; Korey D Conroy
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-12       Impact factor: 15.336

4.  A boronium ion with exceptional electrophilicity.

Authors:  Aleksandrs Prokofjevs; Jeff W Kampf; Edwin Vedejs
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-24       Impact factor: 15.336

5.  Pinacol boronates by direct arene borylation with borenium cations.

Authors:  Alessandro Del Grosso; Paul J Singleton; Christopher A Muryn; Michael J Ingleson
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-05       Impact factor: 15.336

6.  Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors:  Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

7.  N-Directed aliphatic C-H borylation using borenium cation equivalents.

Authors:  Aleksandrs Prokofjevs; Edwin Vedejs
Journal:  J Am Chem Soc       Date:  2011-11-23       Impact factor: 15.419

8.  Borenium ion catalyzed hydroboration of alkenes with N-heterocyclic carbene-boranes.

Authors:  Aleksandrs Prokofjevs; Anne Boussonnière; Linfeng Li; Hélène Bonin; Emmanuel Lacôte; Dennis P Curran; Edwin Vedejs
Journal:  J Am Chem Soc       Date:  2012-07-16       Impact factor: 15.419

9.  Reaction of aminodihydropentalenes with HB(C6F5)2: the crucial role of dihydrogen elimination.

Authors:  Bao-Hua Xu; Gerald Kehr; Roland Fröhlich; Stefan Grimme; Gerhard Erker
Journal:  J Am Chem Soc       Date:  2011-02-18       Impact factor: 15.419

10.  Mechanistic studies into amine-mediated electrophilic arene borylation and its application in MIDA boronate synthesis.

Authors:  Viktor Bagutski; Alessandro Del Grosso; Josue Ayuso Carrillo; Ian A Cade; Matthew D Helm; James R Lawson; Paul J Singleton; Sophia A Solomon; Tommaso Marcelli; Michael J Ingleson
Journal:  J Am Chem Soc       Date:  2012-12-24       Impact factor: 15.419
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  2 in total

1.  Synthesis of Electrophiles Derived from Dimeric Aminoboranes and Assessing Their Utility in the Borylation of π Nucleophiles.

Authors:  Clément R P Millet; Jürgen Pahl; Emily Noone; Kang Yuan; Gary S Nichol; Marina Uzelac; Michael J Ingleson
Journal:  Organometallics       Date:  2022-09-14       Impact factor: 3.837

2.  A family of N-heterocyclic carbene-stabilized borenium ions for metal-free imine hydrogenation catalysis.

Authors:  Jeffrey M Farrell; Roy T Posaratnanathan; Douglas W Stephan
Journal:  Chem Sci       Date:  2015-01-26       Impact factor: 9.825
  2 in total

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