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

Mamoru Tobisu, Takuya Igarashi and Naoto Chatani
Beilstein J. Org. Chem. 2016, 12, 654–661. https://doi.org/10.3762/bjoc.12.65

Supporting Information

Supporting Information File 1: Experimental procedures, data for optimization studies and copies of 1H and 13C NMR spectra.
Format: PDF Size: 6.3 MB Download

Cite the Following Article

Iridium/N-heterocyclic carbene-catalyzed C–H borylation of arenes by diisopropylaminoborane
Mamoru Tobisu, Takuya Igarashi and Naoto Chatani
Beilstein J. Org. Chem. 2016, 12, 654–661. https://doi.org/10.3762/bjoc.12.65

How to Cite

Tobisu, M.; Igarashi, T.; Chatani, N. Beilstein J. Org. Chem. 2016, 12, 654–661. doi:10.3762/bjoc.12.65

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 107.0 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Ramachandran, P. V.; Hamann, H. J.; Mishra, S. Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation. ACS omega 2022, 7, 14377–14389. doi:10.1021/acsomega.2c01461
  • Dang, L.; Huang, G.; Fang, Y.-Q.; Ni, S.-F.; Li, M.-D. Theoretical Study on NHC-Ag(I)/Au(I) Catalyzed Mobius vs Wagner-Meerwein Rearrangements of 2-methyl-N-methoxyaniline. Asian Journal of Organic Chemistry 2021, 10, 3039–3044. doi:10.1002/ajoc.202100456
  • Tian, Y.-M.; Guo, X.-N.; Wu, Z.; Friedrich, A.; Westcott, S. A.; Braunschweig, H.; Radius, U.; Marder, T. B. Ni-Catalyzed Traceless, Directed C3-Selective C-H Borylation of Indoles. Journal of the American Chemical Society 2020, 142, 13136–13144. doi:10.1021/jacs.0c05434
  • Britton, L.; Docherty, J. H.; Dominey, A. P.; Thomas, S. P. Iron-Catalysed C(sp2)-H Borylation Enabled by Carboxylate Activation. Molecules (Basel, Switzerland) 2020, 25, 905. doi:10.3390/molecules25040905
  • Zhao, Q.; Meng, G.; Nolan, S. P.; Szostak, M. N-Heterocyclic Carbene Complexes in C–H Activation Reactions. Chemical reviews 2020, 120, 1981–2048. doi:10.1021/acs.chemrev.9b00634
  • Čubiňák, M.; Edlová, T.; Polák, P.; Tobrman, T. Indolylboronic Acids: Preparation and Applications. Molecules (Basel, Switzerland) 2019, 24, 3523. doi:10.3390/molecules24193523
  • Thongpaen, J.; Manguin, R.; Dorcet, V.; Vives, T.; Duhayon, C.; Mauduit, M.; Baslé, O. Visible Light Induced Rhodium(I)‐Catalyzed C−H Borylation. Angewandte Chemie 2019, 131, 15388–15392. doi:10.1002/ange.201905924
  • Thongpaen, J.; Manguin, R.; Dorcet, V.; Vives, T.; Duhayon, C.; Mauduit, M.; Baslé, O. Visible Light Induced Rhodium(I)‐Catalyzed C−H Borylation. Angewandte Chemie (International ed. in English) 2019, 58, 15244–15248. doi:10.1002/anie.201905924
  • Sipos, G.; Dorta, R. Iridium complexes with monodentate N-heterocyclic carbene ligands. Coordination Chemistry Reviews 2018, 375, 13–68. doi:10.1016/j.ccr.2017.10.019
  • Thongpaen, J.; Schmid, T. E.; Toupet, L.; Dorcet, V.; Mauduit, M.; Baslé, O. Directed ortho C-H borylation catalyzed using Cp*Rh(iii)-NHC complexes. Chemical communications (Cambridge, England) 2018, 54, 8202–8205. doi:10.1039/c8cc03144d
  • Igarashi, T.; Haito, A.; Chatani, N.; Tobisu, M. Nickel-Catalyzed Reductive Cleavage of Carbon–Oxygen Bonds in Anisole Derivatives Using Diisopropylaminoborane. ACS Catalysis 2018, 8, 7475–7483. doi:10.1021/acscatal.8b02009
  • Igarashi, T.; Tobisu, M.; Chatani, N. Catalytic Double Carbon-Boron Bond Formation for the Synthesis of Cyclic Diarylborinic Acids as Versatile Building Blocks for π-Extended Heteroarenes. Angewandte Chemie (International ed. in English) 2017, 56, 2069–2073. doi:10.1002/anie.201612535
  • Igarashi, T.; Tobisu, M.; Chatani, N. Catalytic Double Carbon–Boron Bond Formation for the Synthesis of Cyclic Diarylborinic Acids as Versatile Building Blocks for π‐Extended Heteroarenes. Angewandte Chemie 2017, 129, 2101–2105. doi:10.1002/ange.201612535
  • Furukawa, T.; Tobisu, M.; Chatani, N. C–H Borylation by Platinum Catalysis. Bulletin of the Chemical Society of Japan 2016, 90, 332–342. doi:10.1246/bcsj.20160391
  • Sarpong, R. C-H Functionalization/activation in organic synthesis. Beilstein journal of organic chemistry 2016, 12, 2315–2316. doi:10.3762/bjoc.12.224
  • Tobisu, M.; Igarashi, T.; Chatani, N. Iridium/N‐Heterocyclic Carbene‐Catalyzed C—H Borylation of Arenes by Diisopropylaminoborane. ChemInform 2016, 47. doi:10.1002/chin.201629211
Other Beilstein-Institut Open Science Activities