Au(I)/Au(III)-catalyzed Sonogashira-type reactions of functionalized terminal alkynes with arylboronic acids under mild conditions

Deyun Qian and Junliang Zhang
Beilstein J. Org. Chem. 2011, 7, 808–812. https://doi.org/10.3762/bjoc.7.92

Supporting Information

Supporting information features experimental procedure and spectroscopic data.

Supporting Information File 1: Experimental details and spectra of new compounds.
Format: PDF Size: 811.2 KB Download

Cite the Following Article

Au(I)/Au(III)-catalyzed Sonogashira-type reactions of functionalized terminal alkynes with arylboronic acids under mild conditions
Deyun Qian and Junliang Zhang
Beilstein J. Org. Chem. 2011, 7, 808–812. https://doi.org/10.3762/bjoc.7.92

How to Cite

Qian, D.; Zhang, J. Beilstein J. Org. Chem. 2011, 7, 808–812. doi:10.3762/bjoc.7.92

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

  • Koley, M.; Han, J.; Soloshonok, V. A.; Mojumder, S.; Javahershenas, R.; Makarem, A. External oxidants in gold-catalyzed cross-coupling reactions. Journal of Coordination Chemistry 2023, 77, 1–48. doi:10.1080/00958972.2023.2286182
  • Zhang, L.; Zhang, W.; Li, D.; Yang, R.; Xia, Z. Base-assisted transmetalation enables gold-catalyzed oxidative Sonogashira coupling reaction. iScience 2023, 27, 108531. doi:10.1016/j.isci.2023.108531
  • Nijamudheen, A.; Mandal, N.; Datta, A. doi:10.1002/9783527834242.chf0099
  • Melot, R.; Praveen, C.; Michelet, V. doi:10.1002/9783527834242.chf0098
  • Yasui, M.; Tahara, N.; Matsubara, H.; Takeda, N.; Ueda, M. Gold‐Catalyzed Oxyarylation/Hydroxylation of N‐Alkoxypropiolamides for Chemoselective Synthesis of 4‐Aryl‐3‐(2H)‐isoxazolones. Advanced Synthesis & Catalysis 2022, 364, 3708–3715. doi:10.1002/adsc.202200860
  • Hu, C.; Hashmi, A. S. K. doi:10.1002/9783527834242.chf0161
  • Font, P.; Ribas, X. Fundamental Basis for Implementing Oxidant-Free Au(I)/Au(III) Catalysis. European Journal of Inorganic Chemistry 2021, 2021, 2556–2569. doi:10.1002/ejic.202100301
  • Genoux, A.; Biedrzycki, M.; Merino, E.; Rivera-Chao, E.; Linden, A.; Nevado, C. Synthesis and Characterization of Bidentate (P^N)Gold(III) Fluoride Complexes: Reactivity Platforms for Reductive Elimination Studies. Angewandte Chemie (International ed. in English) 2020, 60, 4164–4168. doi:10.1002/anie.202009359
  • Genoux, A.; Biedrzycki, M.; Merino, E.; Rivera‐Chao, E.; Linden, A.; Nevado, C. Synthesis and Characterization of Bidentate (P^N)Gold(III) Fluoride Complexes: Reactivity Platforms for Reductive Elimination Studies. Angewandte Chemie 2020, 133, 4210–4214. doi:10.1002/ange.202009359
  • Rocchigiani, L.; Bochmann, M. Recent Advances in Gold(III) Chemistry: Structure, Bonding, Reactivity, and Role in Homogeneous Catalysis. Chemical reviews 2020, 121, 8364–8451. doi:10.1021/acs.chemrev.0c00552
  • Abrams, J. N.; K., B. Gold(I)-Catalyzed Cross-Coupling Reactions of Arenediazonium Salts with Alkynoic Acids. Russian Journal of Organic Chemistry 2020, 56, 1236–1244. doi:10.1134/s1070428020070180
  • Sharp-Bucknall, L.; Barwise, L.; Bennetts, J. D.; Albayer, M.; Dutton, J. L. Reactivity Studies of Cationic Au(III) Difluorides Supported by N Ligands. Organometallics 2020, 39, 3344–3351. doi:10.1021/acs.organomet.0c00429
  • Banerjee, S.; Ambegave, S. B.; Mule, R. D.; Senthilkumar, B.; Patil, N. T. Gold-Catalyzed Alkynylative Meyer–Schuster Rearrangement. Organic letters 2020, 22, 4792–4796. doi:10.1021/acs.orglett.0c01596
  • Lakshmipraba, J.; Prabhu, R. N.; Dhayabaran, V. V. (E)-N-(pyren-1-ylmethylene)benzenamine: efficient promoter for additive-free palladium catalyzed aerobic oxidative coupling of arylboronic acids and terminal alkynes. Chemical Papers 2020, 74, 3661–3669. doi:10.1007/s11696-020-01156-8
  • Lakshmipraba, J.; Prabhu, R. N.; Dhayabaran, V. V. Anthracen-9-ylmethylene-(4-methoxyphenyl)amine: efficient promoter for silver-free palladium-catalyzed aerobic oxidative Sonogashira reactions. Transition Metal Chemistry 2020, 45, 325–331. doi:10.1007/s11243-020-00383-y
  • Nijamudheen, A.; Datta, A. Gold-Catalyzed Cross-Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications. Chemistry (Weinheim an der Bergstrasse, Germany) 2019, 26, 1442–1487. doi:10.1002/chem.201903377
  • Mertens, R. T.; Awuah, S. G. ACS Symposium Series - Gold Catalysis: Fundamentals and Recent Developments. ACS Symposium Series; American Chemical Society, 2019; pp 19–55. doi:10.1021/bk-2019-1317.ch002
  • Quillian, B.; Fields, A. E.; Chace, D.; Vickery, A. M.; Sharma, M.; Zurwell, D.; Bazemore, J. G.; Phan, L.; Thomas, D.; Padgett, C. W. Silver triflate mediated dehydration of benzylic alcohols and vinyl hydrovinylation of styrene. Inorganica Chimica Acta 2019, 489, 224–229. doi:10.1016/j.ica.2019.02.015
  • Akram, M. O.; Banerjee, S.; Saswade, S. S.; Bedi, V.; Patil, N. T. Oxidant-free oxidative gold catalysis: the new paradigm in cross-coupling reactions. Chemical communications (Cambridge, England) 2018, 54, 11069–11083. doi:10.1039/c8cc05601c
  • Kang, K.; Liu, S.; Xu, T.; Wang, D.; Leng, X.; Bai, R.; Lan, Y.; Shen, Q. C(sp2)–C(sp2) Reductive Elimination from Well-Defined Diarylgold(III) Complexes. Organometallics 2017, 36, 4727–4740. doi:10.1021/acs.organomet.7b00588

Patents

  • PATIL NITIN TUKARAM; SHAIKH ASLAM CHANDBHAI; KULKARNI PRASAD PADMAKAR; RANADE DNYANESH SADANAND. PYRIDINIUM OXAZOLE DYAD SCAFFOLD AND A PROCESS FOR PREPARATION THEREOF. WO 2018073838 A1, April 26, 2018.
Other Beilstein-Institut Open Science Activities