Literature DB >> 20024326

Ortho-C-H borylation of benzoate esters with bis(pinacolato)diboron catalyzed by iridium-phosphine complexes.

Tatsuo Ishiyama1, Hironori Isou, Takao Kikuchi, Norio Miyaura.   

Abstract

Iridium complexes generated from [Ir(OMe)(COD)](2) and tris[3,5-bis(trifluoromethyl)phenyl]phosphine efficiently catalyzed the ortho-C-H borylation of benzoate esters with bis(pinacolato)diboron in octane at 80 degrees C to produce the corresponding arylboronates in high yields with excellent regioselectivities.

Entities:  

Year:  2009        PMID： 20024326     DOI： 10.1039/b910298a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  21 in total

1.  Arylphosphonate-Directed Ortho C-H Borylation: Rapid Entry into Highly-Substituted Phosphoarenes.

Authors:  Feiyang Xu; Olivia M Duke; Daniel Rojas; Hanka M Eichelberger; Raphael S Kim; Timothy B Clark; Donald A Watson
Journal:  J Am Chem Soc       Date:  2020-07-02       Impact factor: 15.419

Review 2.  Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

Authors:  Brad M Rosen; Kyle W Quasdorf; Daniella A Wilson; Na Zhang; Ana-Maria Resmerita; Neil K Garg; Virgil Percec
Journal:  Chem Rev       Date:  2010-12-06       Impact factor: 60.622

3.  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

4.  Scope of the two-step, one-pot palladium-catalyzed borylation/Suzuki cross-coupling reaction utilizing bis-boronic acid.

Authors:  Gary A Molander; Sarah L J Trice; Steven M Kennedy
Journal:  J Org Chem       Date:  2012-09-20       Impact factor: 4.354

5.  Outer-sphere direction in iridium C-H borylation.

Authors:  Philipp C Roosen; Venkata A Kallepalli; Buddhadeb Chattopadhyay; Daniel A Singleton; Robert E Maleczka; Milton R Smith
Journal:  J Am Chem Soc       Date:  2012-07-03       Impact factor: 15.419

6.  Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene.

Authors:  Tanner W Bingham; Lucas W Hernandez; Daniel G Olson; Riley L Svec; Paul J Hergenrother; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

7.  Ir-Catalyzed ortho-Borylation of Phenols Directed by Substrate-Ligand Electrostatic Interactions: A Combined Experimental/in Silico Strategy for Optimizing Weak Interactions.

Authors:  Buddhadeb Chattopadhyay; Jonathan E Dannatt; Ivonne L Andujar-De Sanctis; Kristin A Gore; Robert E Maleczka; Daniel A Singleton; Milton R Smith
Journal:  J Am Chem Soc       Date:  2017-05-31       Impact factor: 15.419

8.  Achieving High Ortho Selectivity in Aniline C-H Borylations by Modifying Boron Substituents.

Authors:  Milton R Smith; Ranjana Bisht; Chabush Haldar; Gajanan Pandey; Jonathan E Dannatt; Behnaz Ghaffari; Robert E Maleczka; Buddhadeb Chattopadhyay
Journal:  ACS Catal       Date:  2018-05-09       Impact factor: 13.084

9.  Iridium-Catalyzed, Silyl-Directed, peri-Borylation of C-H Bonds in Fused Polycyclic Arenes and Heteroarenes.

Authors:  Bo Su; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-13       Impact factor: 15.336

10.  A traceless directing group for C-H borylation.

Authors:  Sean M Preshlock; Donald L Plattner; Peter E Maligres; Shane W Krska; Robert E Maleczka; Milton R Smith
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-12       Impact factor: 15.336
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