Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors

Morgan Hans, Jan Lorkowski, Albert Demonceau and Lionel Delaude
Beilstein J. Org. Chem. 2015, 11, 2318–2325. https://doi.org/10.3762/bjoc.11.252

Supporting Information

Supporting Information File 1: Full experimental section with detailed synthetic procedures and analytical data for all the compounds.
Format: PDF Size: 3.1 MB Download

Cite the Following Article

Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors
Morgan Hans, Jan Lorkowski, Albert Demonceau and Lionel Delaude
Beilstein J. Org. Chem. 2015, 11, 2318–2325. https://doi.org/10.3762/bjoc.11.252

How to Cite

Hans, M.; Lorkowski, J.; Demonceau, A.; Delaude, L. Beilstein J. Org. Chem. 2015, 11, 2318–2325. doi:10.3762/bjoc.11.252

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.

Citations to This Article

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

Scholarly Works

  • Mazars, F.; Zaragoza, G.; Delaude, L. Synthesis, Characterization, and Catalytic Evaluation of Ruthenium Complexes Bearing Xanthinium-8-dithiocarboxylate Ligands Derived from Caffeine and Theophylline. Organometallics 2024, 43, 2284–2304. doi:10.1021/acs.organomet.4c00315
  • Hanek, K.; Żak, P. Eco-Friendly Functionalization of Ynals with Thiols under Mild Conditions. International journal of molecular sciences 2024, 25, 9201. doi:10.3390/ijms25179201
  • Mermela, A.; Bołt, M.; Mrzygłód, A.; Żak, P. Organocatalytic synthetic route to esters and their application in hydrosilylation process. Scientific reports 2024, 14, 19108. doi:10.1038/s41598-024-70036-y
  • Hanek, K.; Grzegorczyk, K.; Żak, P. NHC‐Rhodium‐Catalyzed Synthesis of Novel Silsesquioxanes Containing S‐Si and S‐Ge Bonds and Their Application in Hydrosilylation Process. ChemCatChem 2024, 16. doi:10.1002/cctc.202301649
  • Hanek, K.; Wałęsa-Chorab, M.; Żak, P. Highly effective synthesis of mercapto-functionalized cubic silsesquioxanes as the first step in designing advanced nano-delivery systems. Inorganic Chemistry Frontiers 2024, 11, 470–477. doi:10.1039/d3qi01838e
  • Bysewski, O.; Klosterhalfen, N.; Jordan, R.; Kletsch, L.; Winter, A.; Klein, A.; Dietzek‐Ivanšić, B.; Schubert, U. S. Luminescent Platinum(II) Complexes with a Tridentate Caffeine‐Based NHC‐Pincer Ligand: Synthesis, Electrochemistry and Photophysics. European Journal of Inorganic Chemistry 2024, 27. doi:10.1002/ejic.202300620
  • Mazars, F.; Etsè, K. S.; Zaragoza, G.; Delaude, L. Pd-PEPPSI catalysts bearing N-heterocyclic carbene ligands derived from caffeine and theophylline for Mizoroki–Heck and C(sp2)–H arylation reactions. Journal of Organometallic Chemistry 2024, 1003, 122928. doi:10.1016/j.jorganchem.2023.122928
  • Touj, N.; Mazars, F.; Zaragoza, G.; Delaude, L. Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes. Beilstein journal of organic chemistry 2023, 19, 1947–1956. doi:10.3762/bjoc.19.145
  • Touj, N.; Taping, J. J.; Tumanov, N.; Wouters, J.; Delaude, L. The Facile Hydrolysis of Imidazolinium Chlorides (N-Heterocyclic Carbene Precursors) Under Basic Aqueous Conditions. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202302402. doi:10.1002/chem.202302402
  • Mazars, F.; Zaragoza, G.; Delaude, L. Synthesis, characterization, and catalytic evaluation of palladium PEPPSI complexes bearing unsymmetrical NHC ligands in Suzuki–Miyaura reactions. Inorganica Chimica Acta 2023, 556, 121676. doi:10.1016/j.ica.2023.121676
  • Park, S.; Kim, Y. Mechanochemical activation of NHC–CS2 adducts for the generation of N‐heterocyclic carbenes. Bulletin of the Korean Chemical Society 2023, 44, 1004–1007. doi:10.1002/bkcs.12782
  • Giarrusso, C. P.; Zeil, D. V.; Blair, V. L. Catalytic exploration of NHC-Ag(I)HMDS complexes for the hydroboration and hydrosilylation of carbonyl compounds. Dalton transactions (Cambridge, England : 2003) 2023, 52, 7828–7835. doi:10.1039/d3dt01042b
  • Mazars, F.; Delaude, L. "Greening" Ruthenium–Arene Catalyst Precursors with N-Heterocyclic Carbene Ligands Derived from Caffeine and Theophylline. Organometallics 2023, 42, 1589–1597. doi:10.1021/acs.organomet.3c00166
  • Bołt, M.; Żak, P. Bulky NHC–Cobalt Complex-Catalyzed Highly Markovnikov-Selective Hydrosilylation of Alkynes. Catalysts 2023, 13, 510. doi:10.3390/catal13030510
  • Bołt, M.; Mermela, A.; Żak, P. Influence of Bis‐NHC Ligand on Platinum‐Catalyzed Hydrosilylation of Internal Alkynes. European Journal of Inorganic Chemistry 2022, 26. doi:10.1002/ejic.202200622
  • Mazars, F.; Zaragoza, G.; Delaude, L. Caffeine and theophylline as sustainable, biosourced NHC ligand precursors for efficient palladium-catalyzed Suzuki–Miyaura cross-coupling reactions. Journal of Organometallic Chemistry 2022, 978, 122489. doi:10.1016/j.jorganchem.2022.122489
  • Bołt, M.; Hanek, K.; Żak, P. Metal-free thioesterification of α,β-unsaturated aldehydes with thiols. Organic Chemistry Frontiers 2022, 9, 4846–4853. doi:10.1039/d2qo00678b
  • Fontes, J. V.; Santos, I. A.; Rosa, L. B.; Lima, R. L. A.; Jardim, A. C. G.; Miguel, D. C.; Abbehausen, C. Antileishmanial and Anti‐Chikungunya Activity of Cu(I)‐N‐Heterocyclic Carbenes. ChemistrySelect 2022, 7. doi:10.1002/slct.202201560
  • Cheng, L.; Deng, L.; Guo, R.; Leng, Y.; Wu, J. Synthesis and Characterization of Heteroleptic Bis-Cyclometalated Iridium(III) Complexes. Journal of Organometallic Chemistry 2022, 972, 122375. doi:10.1016/j.jorganchem.2022.122375
  • Craig, S. M.; Malyk, K. R.; Silk, E. S.; Nakamura, D. T.; Brennessel, W. W.; Kennedy, C. R. Synthesis and characterization of Ni(0) complexes supported by an unsymmetric C,N ligand. Journal of Coordination Chemistry 2022, 75, 1841–1852. doi:10.1080/00958972.2022.2117037
Other Beilstein-Institut Open Science Activities