Literature DB >> 22731752

Iridium-catalyzed, substrate-directed C-H borylation reactions of benzylic amines.

Andrew J Roering1, Lillian V A Hale, Phillip A Squier, Marissa A Ringgold, Emily R Wiederspan, Timothy B Clark.   

Abstract

The iridium-catalyzed arene C-H borylation reaction of benzylic amines has been developed, which inverts the typical steric-controlled product distribution to provide ortho-substituted boronate esters. Picolylamine was found to be an ideal ligand to replace 4,4'-di-tert-butylbipyridine to induce the directing effect. Preliminary experiments are consistent with a mechanism involving dissociation of one amine of the hemilabile diamine ligand.

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Year:  2012        PMID： 22731752     DOI： 10.1021/ol301635x

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


  9 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

2.  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

3.  Cobalt-Catalyzed Borylation of Fluorinated Arenes: Thermodynamic Control of C(sp2)-H Oxidative Addition Results in ortho-to-Fluorine Selectivity.

Authors:  Tyler P Pabst; Jennifer V Obligacion; Étienne Rochette; Iraklis Pappas; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2019-09-16       Impact factor: 15.419

4.  C(sp2)-H Borylation of Fluorinated Arenes Using an Air-Stable Cobalt Precatalyst: Electronically Enhanced Site Selectivity Enables Synthetic Opportunities.

Authors:  Jennifer V Obligacion; Máté J Bezdek; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2017-02-10       Impact factor: 15.419

5.  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

6.  Computational understanding of catalyst-controlled borylation of fluoroarenes: directed vs. undirected pathway.

Authors:  Yu-Hua Liu; Zhong-Jie Jiang
Journal:  RSC Adv       Date:  2020-05-21       Impact factor: 4.036

7.  Silyl phosphorus and nitrogen donor chelates for homogeneous ortho borylation catalysis.

Authors:  Behnaz Ghaffari; Sean M Preshlock; Donald L Plattner; Richard J Staples; Peter E Maligres; Shane W Krska; Robert E Maleczka; Milton R Smith
Journal:  J Am Chem Soc       Date:  2014-10-01       Impact factor: 15.419

8.  Hydrogen Bond Directed ortho-Selective C-H Borylation of Secondary Aromatic Amides.

Authors:  Shao-Tao Bai; Charles B Bheeter; Joost N H Reek
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-17       Impact factor: 15.336

9.  Electronically Driven Regioselective Iridium-Catalyzed C-H Borylation of Donor-π-Acceptor Chromophores Containing Triarylboron Acceptors.

Authors:  Florian Rauch; Johannes Krebs; Julian Günther; Alexandra Friedrich; Martin Hähnel; Ivo Krummenacher; Holger Braunschweig; Maik Finze; Todd B Marder
Journal:  Chemistry       Date:  2020-07-23       Impact factor: 5.236
  9 in total

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