Literature DB >> 28345205

para-Selective C-H Borylation of (Hetero)Arenes by Cooperative Iridium/Aluminum Catalysis.

Lichen Yang1, Kazuhiko Semba1, Yoshiaki Nakao1.   

Abstract

para-Selective C-H borylation of benzamides and pyridines has been achieved by cooperative iridium/aluminum catalysis. A combination of iridium catalysts commonly employed for arene C-H borylation and bulky aluminum-based Lewis acid catalysts provides an unprecedented strategy for controlling the regioselectivity of C-H borylation to give variously substituted (hetero)arylboronates, which are versatile synthetic intermediates for complex multi-substituted aromatic compounds.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C-H activation; Lewis acids; boronate esters; iridium; regioselectivity

Year:  2017        PMID: 28345205     DOI: 10.1002/anie.201701238

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  17 in total

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4.  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
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5.  meta-Selective C-H Borylation of Benzylamine-, Phenethylamine-, and Phenylpropylamine-Derived Amides Enabled by a Single Anionic Ligand.

Authors:  Holly J Davis; Georgi R Genov; Robert J Phipps
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-19       Impact factor: 15.336

6.  Reactivity of highly Lewis acidic diborane(4) towards pyridine and isocyanide: formation of boraalkene-pyridine complex and ortho-functionalized pyridine derivatives.

Authors:  Yuhei Katsuma; Hiroki Asakawa; Makoto Yamashita
Journal:  Chem Sci       Date:  2017-12-11       Impact factor: 9.825

7.  Chromium-catalyzed para-selective formation of quaternary carbon centers by alkylation of benzamide derivatives.

Authors:  Pei Liu; Changpeng Chen; Xuefeng Cong; Jinghua Tang; Xiaoming Zeng
Journal:  Nat Commun       Date:  2018-11-06       Impact factor: 14.919

8.  Rhodium catalyzed template-assisted distal para-C-H olefination.

Authors:  Uttam Dutta; Sudip Maiti; Sandeep Pimparkar; Siddhartha Maiti; Lawrence R Gahan; Elizabeth H Krenske; David W Lupton; Debabrata Maiti
Journal:  Chem Sci       Date:  2019-06-21       Impact factor: 9.825

9.  Base-catalyzed aryl halide isomerization enables the 4-selective substitution of 3-bromopyridines.

Authors:  Thomas R Puleo; Jeffrey S Bandar
Journal:  Chem Sci       Date:  2020-09-09       Impact factor: 9.825

10.  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

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