Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series

Cécile Verrier, Pierrik Lassalas, Laure Théveau, Guy Quéguiner, François Trécourt, Francis Marsais and Christophe Hoarau
Beilstein J. Org. Chem. 2011, 7, 1584–1601. https://doi.org/10.3762/bjoc.7.187

Cite the Following Article

Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series
Cécile Verrier, Pierrik Lassalas, Laure Théveau, Guy Quéguiner, François Trécourt, Francis Marsais and Christophe Hoarau
Beilstein J. Org. Chem. 2011, 7, 1584–1601. https://doi.org/10.3762/bjoc.7.187

How to Cite

Verrier, C.; Lassalas, P.; Théveau, L.; Quéguiner, G.; Trécourt, F.; Marsais, F.; Hoarau, C. Beilstein J. Org. Chem. 2011, 7, 1584–1601. doi:10.3762/bjoc.7.187

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

  • Bakare, S. P.; Patil, M. Ligand Combination Approach in Pd‐Catalyzed Direct C−H Arylation of Benzothiazole and Benzoxazole. European Journal of Organic Chemistry 2023, 27. doi:10.1002/ejoc.202301013
  • Bensalah, D.; Mansour, L.; Sauthier, M.; Gurbuz, N.; Özdemir, I.; Beji, L.; Gatri, R.; Hamdi, N. Plausible PEPPSI catalysts for direct C-H functionalization of five-membered heterocyclic bioactive motifs: synthesis, spectral, X-ray crystallographic characterizations and catalytic activity. RSC advances 2023, 13, 31386–31410. doi:10.1039/d3ra06334h
  • Horký, F.; Schulz, J.; Zábranský, M.; Štěpnička, P. Synthesis and Characterization of Pd(0) Complexes with Electronically Differentiated Ferrocene Diphosphane Ligands. European Journal of Inorganic Chemistry 2023, 26. doi:10.1002/ejic.202300126
  • Joo, J. M. doi:10.1002/9781119774167.ch3
  • Khazipov, O. V.; Shepelenko, K. E.; Soliev, S. B.; Nikolaeva, K. A.; Chernyshev, V. M.; Ananikov, V. P. Optimal Balance in the Catalyst Dynamics Enables C(2)−H Arylation of (Benz)imidazoles and (Benz)oxazoles by an In Situ‐Generated Ni/NHC System. ChemCatChem 2022, 14. doi:10.1002/cctc.202201055
  • Bera, S.; Samanta, R. doi:10.1002/9783527834242.chf0112
  • Kiselev, A. N.; Syrbu, S. A.; Lebedeva, N. S.; Gubarev, Y. A. Functionalization of Porphyrins Using Metal-Catalyzed C–H Activation. Inorganics 2022, 10, 63. doi:10.3390/inorganics10050063
  • Kajol, K.; Kumar, S.; Kumar, A.; Kant, R.; Ramesh, C. Palladium‐Catalyzed Intramolecular C−H Heteroarylation to Access Fused Tricyclic Oxazolo[4,5‐c]Quinolines. Asian Journal of Organic Chemistry 2022, 11. doi:10.1002/ajoc.202200066
  • doi:10.1002/9783527804801.ch8
  • Rossi, R.; Ciofalo, M. Palladium-Catalysed Intermolecular Direct C–H Bond Arylation of Heteroarenes with Reagents Alternative to Aryl Halides: Current State of the Art. Current Organic Chemistry 2022, 26, 215–274. doi:10.2174/1385272826666220201124008
  • Horký, F.; Císařová, I.; Štěpnička, P. Stable Pd(0) Complexes with Ferrocene Bisphosphanes Bearing Phosphatrioxaadamantyl Substituents Efficiently Catalyze Selective C-H Arylation of Benzoxazoles by Aryl Chlorides. ChemCatChem 2021, 13, 4848–4856. doi:10.1002/cctc.202101013
  • Hu, G.; Kitney, S. P.; Liu, Y.; Zhang, K. Synthesis and mesomorphic behavior of novel (bisthiophene)benzene carbazole nematic liquid crystals. Molecular Crystals and Liquid Crystals 2021, 723, 81–92. doi:10.1080/15421406.2021.1895960
  • Hu, G.; Kitney, S. P.; Liu, Y.; Zhang, K. Synthesis and mesomorphic behavior of novel (bisthiophene)benzene carbazole nematic liquid crystals. Molecular Crystals and Liquid Crystals 2021, 1–12.
  • Jagtap, R. A.; Punji, B. Nickel-Catalyzed C-H Bond Functionalization of Azoles and Indoles. Chemical record (New York, N.Y.) 2021, 21, 3573–3588. doi:10.1002/tcr.202100113
  • Piou, T.; Slutskyy, Y.; Kevin, N. J.; Sun, Z.; Xiao, D.; Kong, J. Direct Arylation of Azoles Enabled by Pd/Cu Dual Catalysis. Organic letters 2021, 23, 1996–2001. doi:10.1021/acs.orglett.1c00100
  • Guo, Q.; Tao, L.; Liu, C.; Xiaoyun, Z.; Wan, D.; Zhang, J.; Ai, J.; Li, J. Orientation effects on C2(5)-C2ʹ(5ʹ) linked bioxazole isomers synthesized via regioselective and sequential CH arylation. Chinese Chemical Letters 2021, 32, 425–428. doi:10.1016/j.cclet.2020.05.010
  • Oberheide, A.; Arndt, H.-D. Effective C5‐Arylation of Peptide‐Integrated Oxazoles: Almazole D. Advanced Synthesis & Catalysis 2020, 363, 1132–1136. doi:10.1002/adsc.202001262
  • da Rosa, R.; Grand, L.; Schenkel, E. P.; Bernardes, L. S. C.; Jacolot, M.; Popowycz, F. The Use of 5-Hydroxymethylfurfural towards Fine Chemicals: Synthesis and Direct Arylation of 5-HMF-Based Oxazoles. Synlett 2020, 32, 838–844. doi:10.1055/a-1335-7330
  • Kim, D.; Choi, G.; Kim, W.; Kim, D.-W.; Kang, Y. K.; Hong, S. H. The site-selectivity and mechanism of Pd-catalyzed C(sp2)-H arylation of simple arenes. Chemical science 2020, 12, 363–373. doi:10.1039/d0sc05414c
  • Song, A.-X.; Zeng, X.-X.; Ma, B.-B.; Xu, C.; Liu, F.-S. Direct (Hetero)arylation of Heteroarenes Catalyzed by Unsymmetrical Pd-PEPPSI-NHC Complexes under Mild Conditions. Organometallics 2020, 39, 3524–3534. doi:10.1021/acs.organomet.0c00494

Patents

  • HOVEYDA HAMID; DUTHEUIL GUILLAUME. SYNTHESIS OF 3-METHYL-1,2,4-THIADIAZOLE-5-CARBOHYDRAZIDE OR OF THE METHYL-d3 DEUTERATED FORM THEREOF. WO 2020128003 A1, June 25, 2020.
  • BRUNO NICHOLAS C; BUCHWALD STEPHEN L. Phosphine-ligated palladium sulfonate palladacycles. US 8981086 B2, March 17, 2015.
  • BRUNO NICHOLAS C; BUCHWALD STEPHEN L. Phosphine-ligated palladium sulfonate palladacycles. US 8889857 B2, Nov 18, 2014.
  • BRUNO NICHOLAS C; BUCHWALD STEPHEN L. PHOSPHINE-LIGATED PALLADIUM SULFONATE PALLADACYCLES. WO 2013184198 A1, Dec 12, 2013.
Other Beilstein-Institut Open Science Activities