Highly Efficient Single A³-Coupling (Aldehyde-Amine-Alkyne) Reaction Catalyzed by Air Stable Silver-(N-Heterocyclic Carbene) Complexes: Synthesis and Characterization

References

• A. J. Arduengo, III, R. L. Harlow, and M. Kline, “A Stable Crystalline Carbene,” Journal of the American Chemical Society 113, no. 1 (1991): 361–3.
   Web of Science ®Google Scholar
• Salman A. Khan, Qasim Ullah, Humaira Parveen, Sayeed Mukhtar, Khalid Ahmed Alzahrani, and Mohammad Asad, “Synthesis and Photophysical Investigation of Novel Imidazole Derivative an Efficient Multimodal Chemosensor for Cu(II) and Fluoride Ions,” Journal of Photochemistry and Photobiology A: Chemistry 406 (2021): 113022.
   Web of Science ®Google Scholar
• Abdullah M. Asiri, Najat Saeed M. Al-Ghamdi, Hurija Dzudzevic-Cancar, Parveen Kumar, and Salman A. Khan, “Physicochemical and Photophysical Investigation of Newly Synthesized Carbazole Containing Pyrazoline-Benzothiazole as Fluorescent Chemosensor for the Detection of Cu2+, Fe3+ & Fe2+ Metal Ion,” Journal of Molecular Structure 1195 (2019): 670–80.
   Web of Science ®Google Scholar
• Salman A. Khan, Qasim Ullah, Salahuddin Syed, Alimuddin, Abdulraheem S. A. Almalki, Sanjay Kumar, Rami J. Obaid, Meshari A. Alsharif, S. Y. Alfaifi, and Humaira Parveen, “Microwave Assisted One-Pot Synthesis, Photophysical and Physicochemical Studies of Novel Biologically Active Heterocyclic Donor (D)-π-Acceptor (A) Chromophore,” Bioorganic Chemistry 112 (2021): 104964.
   PubMed Web of Science ®Google Scholar
• Salman A. Khan, Qasim Ullah, Abdulraheem S. A. Almalki, Sanjay Kumar, Rami J. Obaid, Meshari A. Alsharif, S. Y. Alfaifi, and Authar Adil Hashmi, “Synthesis and Photophysical Investigation of (BTHN) Schiff Base as off-on Cd2+ Fluorescent Chemosensor and Its Live Cell Imaging,” Journal of Molecular Liquids 328 (2021): 115407.
   Web of Science ®Google Scholar
• Abdullah M. Asiri, Mona Mohammad Al-Amari, Qasim Ullah, and Salman A. Khan, “Ultrasound-Assisted Synthesis and Photophysical Investigation of a Heterocyclic Alkylated Chalcone: A Sensitive and Selective Fluorescent Chemosensor for Fe3+ in Aqueous Media,” Journal of Coordination Chemistry 73, no. 20–22 (2020): 2987–3002.
   Web of Science ®Google Scholar
• Salman A. Khan, Abdullah M. Asiri, Hadi Mussa Basisi, Mohammad Asad, Mohie E. M. Zayed, Kamlesh Sharma, and Mohmmad Younus Wani, “Synthesis and Evaluation of Quinoline-3-Carbonitrile Derivatives as Potential Antibacterial Agents,” Bioorganic Chemistry 88 (2019): 102968.
   PubMed Web of Science ®Google Scholar
• Paweł Małecki, Katarzyna Gajda, Osman Ablialimov, Maura Malińska, Roman Gajda, Krzysztof Woźniak, Anna Kajetanowicz, and Karol Grela, “Hoveyda–Grubbs-Type Precatalysts with Unsymmetrical N-Heterocyclic Carbenes as Effective Catalysts in Olefin Metathesis,” Organometallics 36, no. 11 (2017): 2153–66.
   Web of Science ®Google Scholar
• G. Meng, and M. Szostak, “Palladium/NHC (NHC = N-Heterocyclic Carbene)-Catalyzed B-Alkyl Suzuki Cross-Coupling of Amides by Selective N–C Bond Cleavage,” Organic Letters 20, no. 21 (2018): 6789–93.
   PubMed Web of Science ®Google Scholar
• X. Tian, J. Lin, S. Zou, J. Lv, Q. Huang, J. Zhu, S. Huang, and Q. Wang, “[Pd (IPr* R)(Acac) Cl]: Efficient Bulky Pd-NHC Catalyst for Buchwald-Hartwig CN Cross-Coupling Reaction,” Journal of Organometallic Chemistry 861 (2018): 125–30.
   Web of Science ®Google Scholar
• M. O. Karataş, S. Günal, A. Mansur, B. Alıcı, and İ. Özdemir, “Catechol‐Bearing Imidazolium and Benzimidazolium Chlorides as Promising Antimicrobial Agents,” Archiv Der Pharmazie 353, no. 6 (2020): 2000013.
   Web of Science ®Google Scholar
• S. Shi, S. P. Nolan, and M. Szostak, “Well-Defined Palladium (II)–NHC Precatalysts for Cross-Coupling Reactions of Amides and Esters by Selective N–C/O–C Cleavage,” Accounts of Chemical Research 51, no. 10 (2018): 2589–99.
   PubMed Web of Science ®Google Scholar
• D. Domyati, R. Latifi, and L. Tahsini, “Sonogashira-Type Cross-Coupling Reactions Catalyzed by Copper Complexes of Pincer N-Heterocyclic Carbenes,” Journal of Organometallic Chemistry 860 (2018): 98–105.
   Web of Science ®Google Scholar
• M. O. Karataş, A. D. Giuseppe, V. Passarelli, B. Alıcı, J. J. Pérez-Torrente, L. A. Oro, İ. Özdemir, and R. Castarlenas, “Pentacoordinated Rhodium (I) Complexes Supported by Coumarin-Functionalized N-Heterocyclic Carbene Ligands,” Organometallics 37, no. 2 (2018): 191–202.
   Web of Science ®Google Scholar
• M. O. Karataş, “Cycloheptyl Substituted N-Heterocyclic Carbene PEPPSI-Type Palladium Complexes with Different N-Coordinated Ligands: Involvement in Suzuki-Miyaura Reaction,” Journal of Organometallic Chemistry 899 (2019): 120906.
   Web of Science ®Google Scholar
• Lamia Boubakri, Khaireddine Dridi, Abdullah Sulaiman Al-Ayed, İsmail Özdemir, Sedat Yasar, and Naceur Hamdi, “Preparation and Characterization of PEPPSI-Palladium N-Heterocyclic Carbene Complexes Using Benzimidazolium Salts Catalyzed Suzuki–Miyaura Cross Coupling Reaction and Their Antitumor and Antimicrobial Activities,” Journal of Coordination Chemistry 72, no. 3 (2019): 516–27.
   Web of Science ®Google Scholar
• M. Benaglia, D. Negri, and G. Dell’Anna, “Enantioselective Addition of Phenyl and Alkyl Acetylenes to Imines Catalyzed by Chiral Cu (I) Complexes,” Tetrahedron Letters 45, no. 47 (2004): 8705–8.
   Web of Science ®Google Scholar
• Vitthalrao S. Kashid, and Maravanji S. Balakrishna, “Microwave-Assisted Copper (I) Catalyzed A3-Coupling Reaction: Reactivity, Substrate Scope and the Structural Characterization of Two Coupling Products,” Catalysis Communications 103 (2018): 78–82.
   Web of Science ®Google Scholar
• C. Wei, and C.-J. Li, “A Highly Efficient Three-Component Coupling of Aldehyde, Alkyne, and Amines via C-H activation catalyzed by gold in water,” Journal of the American Chemical Society 125, no. 32 (2003): 9584–5.
   PubMed Web of Science ®Google Scholar
• V. K.-Y. Lo, Y. Liu, M.-K. Wong, and C.-M. Che, “Gold(III) Salen Complex-Catalyzed Synthesis of Propargylamines via a Three-Component Coupling Reaction,” Organic Letters 8, no. 8 (2006): 1529–32.
   PubMed Web of Science ®Google Scholar
• M. Aliaga-Lavrijsen, R. P. Herrera, M. D. Villacampa, and M. C. Gimeno, “Efficient Gold(I) Acyclic Diaminocarbenes for the Synthesis of Propargylamines and Indolizines,” ACS Omega 3, no. 8 (2018): 9805–13.
   PubMed Web of Science ®Google Scholar
• M. L. Kantam, B. V. Prakash, C. R. V. Reddy, and B. Sreedhar, “Layered Double Hydroxide-Supported Gold Catalyst for Three-Component Aldehyde-Amine-Alkyne Coupling,” Synlett 15, no. 15 (2005): 2329–32.
   Google Scholar
• L. Lili, Z. Xin, G. Jinsen, and X. Chunming, “Engineering Metal–Organic Frameworks Immobilize Gold Catalysts for Highly Efficient One-Pot Synthesis of Propargylamines,” Green Chemistry 14, no. 6 (2012): 1710–20.
   Web of Science ®Google Scholar
• A. Corma, J. Navas, and M. J. Sabater, “Coupling of Two Multistep Catalytic Cycles for the One-Pot Synthesis of Propargylamines from Alcohols and Primary Amines on a Nanoparticulated Gold Catalyst,” Chemistry (Weinheim an Der Bergstrasse, Germany) 18, no. 44 (2012): 14150–6.
   PubMed Web of Science ®Google Scholar
• Gholinejad Mohammad, “Gold Nanoparticles Supported on Imidazole‐Modified Bentonite: Environmentally Benign Heterogeneous Catalyst for the Three‐Component Synthesis of Propargylamines in Water,” ChemPlusChem 83, no. 5 (2018): 431–8.
   PubMed Web of Science ®Google Scholar
• A. S. K. Hashmi, “Gold-Catalyzed Organic Reactions,” Chemical Reviews 107, no. 7 (2007): 3180–211.
   PubMed Web of Science ®Google Scholar
• J. Li, M. Rudolph, F. Rominger, J. Xie, and A. S. K. Hashmi, “A Gold‐Catalyzed A3 Coupling/Cyclization/Elimination Sequence as Versatile Tool for the Synthesis of Furfuryl Alcohol Derivatives from Glyceraldehyde and Alkynes,” Advanced Synthesis & Catalysis 358, no. 2 (2016): 207–11.
   Web of Science ®Google Scholar
• D. Pflästerer, and A. S. K. Hashmi, “Gold Catalysis in Total Synthesis - Recent Achievements,” Chemical Society Reviews 45, no. 5 (2016): 1331–67.
   PubMed Web of Science ®Google Scholar
• C. Wei, Z. Li, and C.-J. Li, “The First Silver-Catalyzed Three-Component Coupling of Aldehyde, Alkyne, and Amine,” Organic Letters 5, no. 23 (2003): 4473–5.
   PubMed Web of Science ®Google Scholar
• E. Loukopoulos, A. Abdul-Sada, E. M. E. Viseux, I. N. Lykakis, and G. E. Kostakis, “Structural Diversity and Catalytic Properties in a Family of Ag (I)-Benzotriazole Based Coordination Compounds,” Crystal Growth & Design 18, no. 9 (2018): 5638–51.
   Web of Science ®Google Scholar
• X. Chen, T. Chen, Y. Zhou, C.-T. Au, L.-B. Han, and S.-F. Yin, “Efficient Synthesis of Propargylamines from Terminal Alkynes, Dichloromethane and Tertiary Amines over Silver Catalysts,” Organic & Biomolecular Chemistry 12, no. 2 (2014): 247–50.
   PubMed Web of Science ®Google Scholar
• Y. He, M.-F. Lv, and C. Cai, “A Simple Procedure for Polymer-Supported N-Heterocyclic Carbene Silver Complex via Click Chemistry: An Efficient and Recyclable Catalyst for the One-Pot Synthesis of Propargylamines,” Dalton Transactions (Cambridge, England: 2003) 41, no. 40 (2012): 12428–33.
   PubMed Web of Science ®Google Scholar
• X. Zhou, Y. Lu, L.-L. Zhai, Y. Zhao, Q. Liu, and W.-Y. Sun, “Propargylamines Formed from Three-Component Coupling Reactions Catalyzed by Silver Oxide Nanoparticles,” RSC Advances 3, no. 6 (2013): 1732–4.
   Web of Science ®Google Scholar
• F. Movahedi, H. Masrouri, and M. Z. Kassaee, “Immobilized Silver on Surface-Modified ZnO Nanoparticles: As an Efficient Catalyst for Synthesis of Propargylamines in Water,” Journal of Molecular Catalysis A: Chemical 395 (2014): 52–7.
   Google Scholar
• S. Díez-González, N. Marion, and S. P. Nolan, “N-Heterocyclic Carbenes in Late Transition Metal Catalysis,” Chemical Reviews 109, no. 8 (2009): 3612–76.
   PubMed Web of Science ®Google Scholar
• D. Munz, “Pushing Electrons—Which Carbene Ligand for Which Application?” Organometallics 37, no. 3 (2018): 275–89.
   Google Scholar
• L. Benhamou, E. Chardon, G. Lavigne, S. Bellemin-Laponnaz, and V. César, “Synthetic Routes to N-Heterocyclic Carbene Precursors,” Chemical Reviews 111, no. 4 (2011): 2705–33.
   PubMed Web of Science ®Google Scholar
• Y. Kim, Y. Kim, M. Y. Hur, and E. Lee, “Efficient Synthesis of Bulky N-Heterocyclic Carbene Ligands for Coinage Metal Complexes,” Journal of Organometallic Chemistry 820 (2016): 1–7.
   Web of Science ®Google Scholar
• M. N. Hopkinson, C. Richter, M. Schedler, and F. Glorius, “An Overview of N-Heterocyclic Carbenes,” Nature 510, no. 7506 (2014): 485–96.
   PubMed Web of Science ®Google Scholar
• P. de Frémont, N. Marion, and S. P. Nolan, “Carbenes: Synthesis, Properties, and Organometallic Chemistry,” Coordination Chemistry Reviews 253, no. 7–8 (2009): 862–1016.
   Web of Science ®Google Scholar
• A. A. Danopoulos, T. Simler, and P. Braunstein, “N-Heterocyclic Carbene Complexes of Copper, Nickel, and Cobalt,” Chemical Reviews 119, no. 6 (2019): 3730–961.
   PubMed Web of Science ®Google Scholar
• D. Bourissou, O. Guerret, F. P. Gabbaï, and G. Bertrand, “Stable Carbenes,” Chemical Reviews 100, no. 1 (2000): 39–92.
   PubMed Web of Science ®Google Scholar
• Zejun Hu, Xufeng Ma, Jiwei Wang, Han Wang, Xiaoyan Han, Min Shi, and Jun Zhang, “Six-Membered Janus-Type Ditopic N-Heterocyclic Carbene Coinage Metal Complexes,” Organometallics 38, no. 9 (2019): 2132–7.
   Web of Science ®Google Scholar
• E. Peris, “Smart N-Heterocyclic Carbene Ligands in Catalysis,” Chemical Reviews 118, no. 19 (2018): 9988–10031.
   PubMed Web of Science ®Google Scholar
• Jitender B. Bariwal, Denis S. Ermolat’ev, and Erik V. Van der Eycken, “Efficient Microwave‐Assisted Synthesis of Secondary Alkylpropargylamines by Using A3‐Coupling with Primary Aliphatic Amines,” Chemistry - A European Journal 16, no. 11 (2010): 3281–4.
   PubMed Web of Science ®Google Scholar
• A. Jenmalm, W. Berts, Y.-L. Li, K. Luthman, I. Csoeregh, and U. Hacksell, “Stereoselective Epoxidation of Phe-Gly and Phe-Phe Vinyl Isosteres,” The Journal of Organic Chemistry 59, no. 5 (1994): 1139–48.
   Web of Science ®Google Scholar
• I. Bolea, A. Gella, and M. Unzeta, “Propargylamine-Derived Multitarget-Directed Ligands: Fighting Alzheimer's Disease with Monoamine Oxidase Inhibitors,” Journal of Neural Transmission (Vienna, Austria: 1996) 120, no. 6 (2013): 893–902.
   PubMed Web of Science ®Google Scholar
• M. Miura, M. Enna, K. Okuro, and M. Nomura, “Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-Buten-3-Yne and 2-Azetidinone Derivatives,” The Journal of Organic Chemistry 60, no. 16 (1995): 4999–5004.
   Web of Science ®Google Scholar
• J. J. Chen, and D. M. Swope, “Clinical Pharmacology of Rasagiline: A Novel, Second-Generation Propargylamine for the Treatment of Parkinson Disease,” The Journal of Clinical Pharmacology 45, no. 8 (2005): 878–94.
   PubMed Web of Science ®Google Scholar
• B. Zhang, and T. Wang, “Gold‐Catalyzed Transformations of Propargyl Alcohols and Propargyl Amines,” Asian Journal of Organic Chemistry 7, no. 9 (2018): 1758–83.
   Web of Science ®Google Scholar
• G. Hooyberghs, S. Van Hove, J. Jacobs, L. Van Meervelt, and E. V. Van der Eycken, “A One-Pot Synthesis of Triazolodiazepines,” European Journal of Organic Chemistry 21 (2015): 4726–31.
   Google Scholar
• R. P. Herrera, and M. L. Eugenia, Multicomponent Reactions: Concepts and Applications for Design and Synthesis (New York: John Wiley & Sons, 2015).
   Google Scholar
• V. A. Peshkov, O. P. Pereshivko, and E. V. Van der Eycken, “A Walk Around the A3-Coupling,” Chemical Society Reviews 41, no. 10 (2012): 3790–807.
   PubMed Web of Science ®Google Scholar
• (a) S. Cheng, N. Shang, C. Feng, S. Gao, C. Wang, and Z. Wang, “Efficient Multicomponent Synthesis of Propargylamines Catalyzed by Copper Nanoparticles Supported on Metal-Organic Framework Derived Nanoporous Carbon,” Catalysis Communications 89 (2017): 91–5.
   Web of Science ®Google Scholar
  (b) M. Varyani, P. K. Khatri, and S. L. Jain, “Amino Acid Ionic Liquid Bound Copper Schiff Base Catalyzed Highly Efficient Three Component A3-Coupling Reaction,” Catalysis Communications 77 (2016): 113–7.
   Web of Science ®Google Scholar
  (c) M. Islam, A. S. Roy, and S. M. Islam, “Functionalized Polystyrene Supported Copper (I) Complex as an Effective and Reusable Catalyst for Propargylamines Synthesis in Aqueous Medium,” Catalysis Letters 146, no. 6 (2016): 1128–38.
   Web of Science ®Google Scholar
  (d) Shweta Kumari, Amiya Shekhar, and Devendra D. Pathak, “Synthesis and Characterization of a Cu(ii) Schiff base Complex Immobilized on Graphene Oxide and its Catalytic Application in the Green Synthesis of Propargylamines,” RSC Advances 6, no. 19 (2016): 15340–4.
   Web of Science ®Google Scholar
  (g) Z. L. Palchak, D. J. Lussier, C. J. Pierce, and C. H. Larsen, “Synthesis of Tetrasubstituted Propargylamines from Cyclohexanone by Solvent-Free Copper(II) Catalysis,” Green Chemistry 17, no. 3 (2015): 1802–10.
   Web of Science ®Google Scholar
  (e) M. Gholinejad, F. Saadati, S. Shaybanizadeh, and B. Pullithadathilc, “Green Synthesis of Au Nanoparticles Using an Aqueous Extract of Stachys Lavandulifolia and Their Catalytic Performance for Alkyne/Aldehyde/Amine A3 Coupling Reactions,” RSC Advances 8, no. 67 (2018): 38186–95.
   Web of Science ®Google Scholar
  (f) Morteza Abdoli, Hamid Saeidian, and Ali Kakanejadifard, “Highly Efficient One-Pot Synthesis of Novel Propargylamine-Based Sulfonamides by an A3-Coupling Reaction,” Synlett 27, no. 17 (2016): 2473–6.
   Web of Science ®Google Scholar
  (g) P. Li, S. Regati, H.-C. Huang, H. D. Arman, B.-L. Chen, and J. C.-G. Zhao, “A Sulfonate-Based Cu (I) metal-Organic Framework as a Highly Efficient and Reusable Catalyst for the Synthesis of Propargylamines under Solvent-Free Conditions,” Chinese Chemical Letters 26, no. 1 (2015): 6–10.
   Web of Science ®Google Scholar
  (h) B. Kodicherla, P. C. Perumgani, and M. R. Mandapati, “Polymer‐Anchored Copper (II) Complex: An Efficient Reusable Catalyst for the Synthesis of Propargylamines,” Applied Organometallic Chemistry 28, no. 10 (2014): 756–9.
   Web of Science ®Google Scholar
  (i) M. Abdollahi-Alibeik, and A. Moaddeli, “Copper Modified Spherical MCM-41 Nano Particles: An Efficient Catalyst for the Three-Component Coupling of Aldehydes, Amines and Alkynes in Solvent-Free Conditions,” RSC Advances 4, no. 75 (2014): 39759–66.
   Web of Science ®Google Scholar
  (j) S. Nakamura, M. Ohara, Y. Nakamura, N. Shibata, and T. Toru, “Copper‐Catalyzed Enantioselective Three‐Component Synthesis of Optically Active Propargylamines from Aldehydes, Amines, and Aliphatic Alkynes,” Chemistry - A European Journal 16, no. 8 (2010): 2360–2.
   PubMed Web of Science ®Google Scholar
  (k) M. K. Patil, M. Keller, B. M. Reddy, P. Pale, and J. Sommer, “Copper Zeolites as Green Catalysts for Multicomponent Reactions of Aldehydes, Terminal Alkynes and Amines: An Efficient and Green Synthesis of Propargylamines,” European Journal of Organic Chemistry 2008, no. 26 (2008): 4440–5.
   Web of Science ®Google Scholar
  (l) Jitender B. Bariwal, Denis S. Ermolat'ev, and Erik V. Van der Eycken, “Efficient Microwave‐Assisted Synthesis of Secondary Alkylpropargylamines by Using A3‐Coupling with Primary Aliphatic Amines,” Chemistry - A European Journal 16, no. 11 (2010): 3281–4.
   PubMed Web of Science ®Google Scholar
  (m) A. Fodor, A. Kiss, N. Debreczeni, Z. Hell, and I. Gresits, “A Simple Method for the Preparation of Propargylamines Using Molecular Sieve Modified with Copper(II),” Organic & Biomolecular Chemistry 8, no. 20 (2010): 4575–81.
   PubMed Web of Science ®Google Scholar
  (n) H.-B. Chen, Y. Zhao, and Y. Liao, “Aldehyde–Alkyne–Amine (A3) Coupling Catalyzed by a Highly Efficient Dicopper Complex,” RSC Advances 5, no. 47 (2015): 37737–41.
   Web of Science ®Google Scholar
  (o) Boyapati M. Choudary, Chidara. Sridhar, Mannepalli L. Kantam, and Bojja Sreedhar, “Hydroxyapatite Supported Copper Catalyst for Effective Three-Component Coupling,” Tetrahedron Letters 45, no. 39 (2004): 7319–21.
   Web of Science ®Google Scholar
  (p) Lei Shi, Yong-Qiang Tu, Min Wang, Fu-Min Zhang, and Chun-An Fan, “Microwave-Promoted Three-Component Coupling of Aldehyde, Alkyne, and Amine via C-H Activation Catalyzed by Copper in Water,” Organic Letters 6, no. 6 (2004): 1001–3.
   PubMed Web of Science ®Google Scholar
  (q) S. B. Park, and H. Alper, “An Efficient Synthesis of Propargylamines via C–H Activation Catalyzed by Copper (I) in Ionic Liquids,” Chemical Communications 10, no. 10 (2005): 1315–7.
   Google Scholar
  (r) H. Naeimi, and M. Moradian, “Encapsulation of Copper (I)-Schiff Base Complex in NaY Nanoporosity: An Efficient and Reusable Catalyst in the Synthesis of Propargylamines via A3-Coupling (Aldehyde-Amine-Alkyne) Reactions,” Applied Catalysis A: General 467 (2013): 400–6.
   Web of Science ®Google Scholar
  (s) M. Wang, P. Li, and L. Wang, “Silica‐Immobilized NHC–CuI Complex: An Efficient and Reusable Catalyst for A3‐Coupling (Aldehyde–Alkyne–Amine) under Solventless Reaction Conditions,” European Journal of Organic Chemistry 2008 (2008): 2255–61.
   Web of Science ®Google Scholar
  (t) M. J. Aliaga, D. J. Ramón, and M. Yus, “Impregnated Copper on Magnetite: An Efficient and Green Catalyst for the Multicomponent Preparation of Propargylamines under Solvent Free Conditions,” Organic & Biomolecular Chemistry 8, no. 1 (2010): 43–6.
   PubMed Web of Science ®Google Scholar
• Y. Li, X. Chen, Y. Song, L. Fang, and G. Zou, “Well-Defined N-Heterocyclic Carbene Silver Halides of 1-Cyclohexyl-3-Arylmethylimidazolylidenes: Synthesis, Structure and Catalysis in A3-Reaction of Aldehydes, Amines and Alkynes,” Dalton Transactions (Cambridge, England: 2003) 40, no. 9 (2011): 2046–52.
   PubMed Web of Science ®Google Scholar
• C. Saturnino, I. Barone, D. Iacopetta, A. Mariconda, M. S. Sinicropi, C. Rosano, A. Campana, S. Catalano, P. Longo, and S. Ando, “N-Heterocyclic Carbene Complexes of Silver and Gold as Novel Tools against Breast Cancer Progression,” Future Medicinal Chemistry 8, no. 18 (2016): 2213–29.
   PubMed Web of Science ®Google Scholar
• Domenico Iacopetta, Annaluisa Mariconda, Carmela Saturnino, Anna Caruso, Giuseppe Palma, Jessica Ceramella, Noemi Muià, Mariarita Perri, Maria Stefania Sinicropi, Maria Cristina Caroleo, et al. “Novel Gold and Silver Carbene Complexes Exert Antitumor Effects Triggering the Reactive Oxygen Species Dependent Intrinsic Apoptotic Pathway,” Chemmedchem 12, no. 24 (2017): 2054–65.
   PubMed Web of Science ®Google Scholar
• M. Napoli, C. Saturnino, E. I. Cianciulli, M. Varcamonti, A. Zanfardino, G. Tommonaro, and P. Longo, “Silver (I) N-Heterocyclic Carbene Complexes: Synthesis, Characterization and Antibacterial Activity,” Journal of Organometallic Chemistry 725 (2013): 46–53.
   Web of Science ®Google Scholar
• P. O. Asekunowo, R. A. Haque, and M. R. Razali, “Sterically Modulated Silver (I) complexes of N-Benzyl-Substituted N-Heterocyclic Carbenes: Synthesis, Crystal Structures and Bioactivity,” Transition Metal Chemistry 40, no. 1 (2015): 79–88.
   Web of Science ®Google Scholar
• Yali Han, Zhenzhen Tian, Shumiao Zhang, Xicheng Liu, Juanjuan Li, Yanru Li, Yi Liu, Min Gao, and Zhe Liu, “Half-Sandwich IridiumIIIN-Heterocyclic Carbene Antitumor Complexes and Biological Applications,” Journal of Inorganic Biochemistry 189 (2018): 163–71.
   PubMed Web of Science ®Google Scholar
• Q. Liu, H. Wu, Z. Zhao, and D. Wei, “Macrometallocycle Binuclear NHC Silver(I) complex with Bridging Azobenzene: Synthesis, Structure and Recognition for Hydrogen Sulfate,” Tetrahedron 75, no. 23 (2019): 3128–34.
   Web of Science ®Google Scholar
• Deniz Demir Atli. “Synthesis and Catalytic Application of Cyclopentadienyl Nickel(II) N-Heterocyclic Carbene Complexes,” Journal of Coordination Chemistry 73, no. 10 (2020): 1530–7.
   Web of Science ®Google Scholar
• N. Hall, “Chemists Clean up Synthesis with One-Pot Reactions,” Science (New York, N.Y.) 266, no. 5182 (1994): 32–5.
   PubMed Web of Science ®Google Scholar
• Alexander Dömling, Eberhardt Herdtweck, Ivar Ugi, Larry L. Miller, Giovanni V. Sebastiani, George W. Francis, József Szúnyog, and Bengt Långström, “MCR V: The Seven-Component Reaction,” Acta Chemica Scandinavica 52 (1998): 107–13.
   Google Scholar
• B. M. Trost, “The Atom Economy-A Search for Synthetic Efficiency,” Science (New York, N.Y.) 254, no. 5037 (1991): 1471–7.
   PubMed Web of Science ®Google Scholar
• J. H. Zhang, C. M. Wei, and C. J. Li, “Cu (I) Br Mediated Coupling of Alkynes with N-Acylimine and N-Acyliminium Ions in Water,” Tetrahedron Letters 43, no. 33 (2002): 5731–3.
   Web of Science ®Google Scholar
• Ming-Tsz Chen, Brant Landers, and Oscar Navarro, “Well-Defined (N-Heterocyclic Carbene)–Ag (I) complexes as Catalysts for A3 Reactions,” Organic & Biomolecular Chemistry 10, no. 11 (2012): 2206–8.
   PubMed Web of Science ®Google Scholar
• B. Landers, and O. Navarro, “Microwave‐Assisted Synthesis of (N‐Heterocyclic Carbene) MCl Complexes of Group 11 Metals,” European Journal of Inorganic Chemistry 18 (2012): 2980–2.
   Google Scholar
• Cécilia A. Citadelle, Erwan Le Nouy, Fabrice Bisaro, Alexandra M. Z. Slawin, and Catherine S. J. Cazin, “Simple and Versatile Synthesis of Copper and Silver N-Heterocyclic Carbene Complexes in Water or Organic Solvents,” Dalton Transactions (Cambridge, England: 2003) 39, no. 19 (2010): 4489–91.
   PubMed Web of Science ®Google Scholar
• J.-J. Chen, Z.-L. Gan, Q. Huang, and X.-Y. Yi, “Well-Defined Dinuclear Silver Phosphine Complexes Based on Nitrogen Donor Ligand and Their High Efficient Catalysis for A3-Coupling Reaction,” Inorganica Chimica Acta 466 (2017): 93–9.
   Web of Science ®Google Scholar
• Naghmeh Esfandiary, Farzane Pazoki, Athar Nakisa, Kobra Azizi, Iman Radfar, and Akbar Heydari, “Silver Chloride Supported on Vitamin B1–Organometallic Magnetic Catalyst: Synthesis, Density Functional Theory Study and Application in A3-Coupling Reactions,” Applied Organometallic Chemistry 34, no. 8 (2020): e5725.
   Web of Science ®Google Scholar
• M. Gholinejad, M. Afrasi, and C. Najera, “Caffeine Gold Complex Supported on Magnetic Nanoparticles as a Green and High Turnover Frequency Catalyst for Room Temperature A3 Coupling Reaction in Water,” Applied Organometallic Chemistry 33, no. 4 (2019): e4760.
   Web of Science ®Google Scholar