Literature DB >> 26371538

C-H functionalization at sterically congested positions by the platinum-catalyzed borylation of arenes.

Takayuki Furukawa1, Mamoru Tobisu2, Naoto Chatani1.   

Abstract

Despite significant progress in the area of C-H bond functionalization of arenes, no general method has been reported for the functionalization of C-H bonds at the sterically encumbered positions of simple arenes, such as mesitylene. Herein, we report the development of the first platinum-based catalyst for C-H borylation of arenes and heteroarenes. Notably, this method exhibited high tolerance toward steric hindrance and provided rapid access to a series of 2,6-disubstituted phenylboronic esters, valuable building blocks for further elaborations.

Entities:  

Year:  2015        PMID: 26371538     DOI: 10.1021/jacs.5b07677

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  15 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.  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

3.  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

Review 4.  N-Heterocyclic Carbene Complexes in C-H Activation Reactions.

Authors:  Qun Zhao; Guangrong Meng; Steven P Nolan; Michal Szostak
Journal:  Chem Rev       Date:  2020-01-22       Impact factor: 60.622

5.  meta-Selective C-H Arylation of Fluoroarenes and Simple Arenes.

Authors:  Luo-Yan Liu; Jennifer X Qiao; Kap-Sun Yeung; William R Ewing; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-09       Impact factor: 15.336

6.  Mechanistic Origins of Regioselectivity in Cobalt-Catalyzed C(sp2)-H Borylation of Benzoate Esters and Arylboronate Esters.

Authors:  Tyler P Pabst; Linda Quach; Kaitlyn T MacMillan; Paul J Chirik
Journal:  Chem       Date:  2020-12-09       Impact factor: 22.804

7.  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

Review 8.  Catalysis using transition metal complexes featuring main group metal and metalloid compounds as supporting ligands.

Authors:  Jun Takaya
Journal:  Chem Sci       Date:  2020-09-10       Impact factor: 9.825

9.  Iridium/N-heterocyclic carbene-catalyzed C-H borylation of arenes by diisopropylaminoborane.

Authors:  Mamoru Tobisu; Takuya Igarashi; Naoto Chatani
Journal:  Beilstein J Org Chem       Date:  2016-04-07       Impact factor: 2.883

10.  Cationic Pd(II)-catalyzed C-H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies.

Authors:  Takashi Nishikata; Alexander R Abela; Shenlin Huang; Bruce H Lipshutz
Journal:  Beilstein J Org Chem       Date:  2016-05-20       Impact factor: 2.883

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