Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 52, 2022 - Issue 22
287
Views
2
CrossRef citations to date
0
Altmetric
Articles

2,2’-Dipyridylamine: A tripod ligand enabling practical access to diaryl ethers via Cu-catalyzed coupling reaction

ORCID Icon, , , & ORCID Icon
Pages 2163-2170 | Received 15 Mar 2022, Published online: 20 Oct 2022

References

  • (a) Theil, F. Synthesis of Diaryl Ethers: A Long-Standing Problem Has Been Solved. Angew. Chem. Int. Ed 1999, 38, 2345–2347. DOI: 10.1002/(SICI)1521-3773(19990816)38:16<2345::AID-ANIE2345>3.0.CO;2-5. (b) Saywer, J. S. Tetrahedron. 2000, 56, 5045. (c) Boger, D. L.; Miyazaki, S.; Kim, S. H.; Wu, J. H.; Castle, S. L.; Loiseleur, O.; Jin, Q. Total Synthesis of the Vancomycin Aglycon. J. Am. Chem. Soc. 1999, 121, 10004–10011. DOI: 10.1021/ja992577q.
  • Chekal, B. P.; Guinness, S. M.; Lillie, B. M.; McLaughlin, R. W.; Palmer, C. W.; Post, R. J.; Sieser, J. E.; Singer, R. A.; Sluggett, G. W.; Vaidyanathan, R.; Withbroe, G. J. Development of an Efficient Pd-Catalyzed Coupling Process for Axitinib. Org. Process Res. Dev. 2014, 18, 266–274. DOI: 10.1021/op400088k.
  • Hughes, D. L. Patent Review of Manufacturing Routes to Recently Approved Oncology Drugs: Ibrutinib, Cobimetinib, and Alectinib. Org. Process Res. Dev. 2016, 20, 1855–1869. DOI: 10.1021/acs.oprd.6b00304.
  • Takashima-Hirano, M.; Shukuri, M.; Takashima, T.; Goto, M.; Wada, Y.; Watanabe, Y.; Onoe, H.; Doi, H.; Suzuki, M. General Method for the (11)C-Labeling of 2-Arylpropionic Acids and Their Esters: construction of a PET Tracer Library for a Study of Biological Events Involved in COXs Expression. Chemistry. 2010, 16, 4250–4258. DOI: 10.1002/chem.200903044.
  • Evans, D. A.; Ellman, J. A. The Total Syntheses of the Isodityrosine-Derived Cyclic Tripeptides OF4949-III and K-13. Determination of the Absolute Configuration of K-13. J. Am. Chem. So.c 1989, 111, 1063–1072. DOI: 10.1021/ja00185a042.
  • Xing, X.; Padmanaban, D.; Yeh, L.; Cuny, G. D. Utilization of a Copper-Catalyzed Diaryl Ether Synthesis for the Preparation of Verbenachalcone. Tetrahedron. 2002, 58, 7903–7910. DOI: 10.1016/S0040-4020(02)00915-8.
  • Lindley, J. Tetrahedron Report Number 163. Tetrahedron. 1984, 40, 1433–1456. DOI: 10.1016/S0040-4020(01)91791-0.
  • Moroz, A. A.; Shvartsberg, M. S. The Ullmann Ether Condensation. Russ. Chem. Rev 1974, 43, 679–689. DOI: 10.1070/RC1974v043n08ABEH001845.
  • (a) Gujadher, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4135. (b) Wolter, M.; Nordman, G.; Job, G. E.; Buchwald, S. L. Copper-Catalyzed Coupling of Aryl Iodides with Aliphatic Alcohols. Org. Lett. 2002, 4, 973–976. DOI: 10.1021/ol025548k. (c) Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. Using Intelligent/Random Library Screening to Design Focused Libraries for the Optimization of Homogeneous Catalysts: Ullmann Ether Formation. J. Am. Chem. Soc. 2000, 122, 5043–5051. DOI: 10.1021/ja000094c.
  • (a) Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623. DOI: 10.1021/ol025839t. (b) Goodbrand, H. B.; Hu, N.-X. Ligand-Accelerated Catalysis of the Ullmann Condensation: Application to Hole Conducting Triarylamines. J. Org. Chem. 1999, 64, 670–674. DOI: 10.1021/jo981804o. (c) Lu, Z.; Twieg, R. J.; Huang, S. D. Copper-Catalyzed Amination of Aromatic Halides with 2-N,N-Dimethylaminoethanol as Solvent. Tetrahedron Lett 2003, 44, 6289–6292. DOI: 10.1016/S0040-4039(03)01536-3.
  • (a) Oi, R.; Shimakawa, C.; Takenaka, S. Chem. Lett. 1988, 5, 899. (b) Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. Using Intelligent/Random Library Screening to Design Focused Libraries for the Optimization of Homogeneous Catalysts: Ullmann Ether Formation. J. Am. Chem. Soc. 2000, 122, 5043–5051. DOI: 10.1021/ja000094c. (c) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. A General Copper-Catalyzed Synthesis of Diaryl Ethers. J. Am. Chem. Soc. 1997, 119, 10539–10540. DOI: 10.1021/ja971901j. (d) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Formation of Aryl-Nitrogen, Aryl-Oxygen, and Aryl-Carbon Bonds Using Well-Defined Copper(I)-Based Catalysts. Org. Lett. 2001, 3, 4315–4317. DOI: 10.1021/ol0170105.
  • (a) Gujadhur, R. K.; Venkataraman, D. Synthesis of Diaryl Ethers Using an Easy-to-Prepare, Air-Stable, Soluble Copper(I) CATALYST. Synth. Commun. 2001, 31, 2865–2879. DOI: 10.1081/SCC-100105338. (b) Weingarten, H. Mechanism of the Ullmann Condensation 1. J. Org. Chem. 1964, 29, 3624–3626.
  • (a) Cristau, H.; Cellier, P. P.; Hamada, S.; Spindler, J.; Taillefer, M. A General and Mild Ullmann-Type Synthesis of Diaryl Ethers. Org. Lett. 2004, 6, 913–916. DOI: 10.1021/ol036290g. (b) Ouali, A.; Spindler, J.; Cristau, H.; Taillefer, M. A. Mild Conditions for Copper-Catalyzed Coupling Reaction of Phenols and Aryl Iodides and Bromides. Adv. Synth. Catal. 2006, 348, 499–505. DOI: 10.1002/adsc.200505385. (c) Ma, D.; Cai, Q. N,N-Dimethyl Glycine-Promoted Ullmann Coupling Reaction of Phenols and Aryl Halides. Org Lett. 2003, 5, 3799–3802. DOI: 10.1021/ol0350947. (d) Debabrata, M.; Stephen, L. B. J. Org. Chem 2010, 75, 191.
  • Chan, D. M. T.; Monaco, K. L.; Li, R.; Bonne, D.; Clark, C. G.; Lam, P. Y. S. Copper Promoted C—N and C—O Bond Cross-Coupling with Phenyl and Pyridylboronates. Tetrahedron. Lett. 2003, 44, 3863–3865. DOI: 10.1016/S0040-4039(03)00739-1.
  • Evans, D. A.; Katz, J. L.; West, T. R. Synthesis of Diaryl Ethers through the Copper-Promoted Arylation of Phenols with Arylboronic Acids. An Expedient Synthesis of Thyroxine. Tetrahedron. Lett. 1998, 39, 2937–2940. DOI: 10.1016/S0040-4039(98)00502-4.
  • Quach, T. D.; Batey, R. A. Copper(II)-Catalyzed Ether Synthesis from Aliphatic Alcohols and Potassium Organotrifluoroborate Salts. Org. Lett. 2003, 5, 1381–1384. DOI: 10.1021/ol034454n.
  • (a) Barton, D. H. R.; Finet, J.-P.; Khamsi, J.; Pichon, C. Copper Catalysed -Phenylation of Phenols and Enols by Pentavalent Organobismuth Compounds. Tetrahedron. Lett. 1986, 27, 3619–3622. DOI: 10.1016/S0040-4039(00)84864-9. (b) Barton, D. H. R.; Finet, J.-P.; Khamsi, J. Copper Salts Catalysis of N-Phenylation of Amines by Trivalent Organobismuth Compounds. Tetrahedron. Lett. 1987, 28, 887–890. DOI: 10.1016/S0040-4039(01)81015-7.
  • (a) Ribeiro, G. H.; Colina-Vegas, L.; Clavijo, J. C. T.; Ellena, J.; Cominetti, M. R.; Batista, A. A. Ru(II)/N-N/PPh3 Complexes as Potential Anticancer Agents against MDA-MB-231 Cancer Cells (N-N = Diimine or Diamine). J. Inorg. Biochem. 2019, 193, 70–83. DOI: 10.1016/j.jinorgbio.2019.01.006. (b) Bulatov, E.; Haukka, M. Non-Conventional Synthesis and Photophysical Studies of Platinum(ii) Complexes with Methylene Bridged 2,2'-Dipyridylamine Derivatives. Dalton. Trans. 2019, 48, 3369–3379. DOI: 10.1039/c8dt03912g. (c) Chandra, S.; Iqbal, M. M.; Bhattacharya, A. J. Chem. Sci (Berlin, Germany). 2016, 128, 1175.
  • Zhu, H.; Xu, J.; Varlashkin, P.; Long, S.; Kidd, C. Dehydration, Hydration Behavior, and Structural Analysis of Fenoprofen Calcium. J. Pharm. Sci. 2001, 90, 845–859. DOI: 10.1002/jps.1038.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.