{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,11]],"date-time":"2026-10-11T02:19:08Z","timestamp":1791685148816,"version":"4.3.4"},"reference-count":90,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2020,7,9]],"date-time":"2020-07-09T00:00:00Z","timestamp":1594252800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Medium-sized heterocycles (with 8 to 11 atoms) constitute important structural components of several biologically active natural compounds and represent promising scaffolds in medicinal chemistry. However, they are under-represented in the screening of chemical libraries as a consequence of being difficult to access. In particular, methods involving intramolecular bond formation are challenging due to unfavorable enthalpic and entropic factors, such as transannular interactions and conformational constraints. The present review focuses on the synthesis of medium-sized heterocycles by transition-metal-catalyzed intramolecular cyclization, which despite its drawbacks remains a straightforward and attractive synthesis strategy. The obtained heterocycles differ in their nature, number of heteroatoms, and ring size. The methods are classified according to the metal used (palladium, copper, gold, silver), then subdivided according to the type of bond formed, namely carbon\u2013carbon or carbon\u2013heteroatom.<\/jats:p>","DOI":"10.3390\/molecules25143147","type":"journal-article","created":{"date-parts":[[2020,7,10]],"date-time":"2020-07-10T09:45:31Z","timestamp":1594374331000},"page":"3147","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":95,"title":["Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization"],"prefix":"10.3390","volume":"25","author":[{"given":"Mickael","family":"Choury","sequence":"first","affiliation":[{"name":"Universit\u00e9 de Strasbourg, CNRS, Laboratoire d\u2019Innovation Th\u00e9rapeutique, LIT UMR 7200, F-67000 Strasbourg, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexandra","family":"Basilio Lopes","sequence":"additional","affiliation":[{"name":"Universit\u00e9 de Strasbourg, CNRS, Laboratoire d\u2019Innovation Th\u00e9rapeutique, LIT UMR 7200, F-67000 Strasbourg, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9144-0295","authenticated-orcid":false,"given":"Ga\u00eblle","family":"Blond","sequence":"additional","affiliation":[{"name":"Universit\u00e9 de Strasbourg, CNRS, Laboratoire d\u2019Innovation Th\u00e9rapeutique, LIT UMR 7200, F-67000 Strasbourg, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2945-0078","authenticated-orcid":false,"given":"Mihaela","family":"Gulea","sequence":"additional","affiliation":[{"name":"Universit\u00e9 de Strasbourg, CNRS, Laboratoire d\u2019Innovation Th\u00e9rapeutique, LIT UMR 7200, F-67000 Strasbourg, France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,7,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2127","DOI":"10.1021\/cr020095i","article-title":"Transition-Metal-Catalyzed Reactions in Heterocyclic Synthesis","volume":"104","author":"Nakamura","year":"2004","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3084","DOI":"10.1021\/cr300333u","article-title":"Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles","volume":"113","author":"Gulevich","year":"2013","journal-title":"Chem. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"319","DOI":"10.1016\/B978-0-08-040589-6.50022-9","article-title":"Eight-Membered and Larger Rings","volume":"Volume 3","author":"Suschitzky","year":"1991","journal-title":"Progress in Heterocyclic Chemistry"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1039\/9781847556332-00455","article-title":"Eight-Membered and Larger Rings Systems","volume":"Volume 5","author":"Suschitzky","year":"1986","journal-title":"Heterocyclic Chemistry"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1021\/ar00064a001","article-title":"Ring Closure Reactions of Bifunctional Chain Molecules","volume":"14","author":"Illuminati","year":"1981","journal-title":"Acc. Chem. Res."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"3117","DOI":"10.1002\/1099-0690(200009)2000:18<3117::AID-EJOC3117>3.0.CO;2-5","article-title":"The Role of Ring Strain on the Ease of Ring Closure of Bifunctional Chain Molecules","volume":"2000","author":"Galli","year":"2000","journal-title":"Eur. J. Org. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2073","DOI":"10.1002\/1521-3773(20000616)39:12<2073::AID-ANIE2073>3.0.CO;2-0","article-title":"Synthesis of Medium-Sized Rings by the Ring-Closing Metathesis Reaction","volume":"39","author":"Maier","year":"2000","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"5740","DOI":"10.1002\/anie.200600787","article-title":"Selective Construction of Carbocyclic Eight-Membered Rings by Ring-Closing Metathesis of Acyclic Precursors","volume":"45","author":"Michaut","year":"2006","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"3919","DOI":"10.1016\/j.tet.2007.01.063","article-title":"Formation of medium-ring heterocycles by diene and enyne metathesis","volume":"63","author":"Chattopadhyay","year":"2007","journal-title":"Tetrahedron"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"9349","DOI":"10.1016\/S0040-4020(99)00483-4","article-title":"Free Radicals in the Synthesis of Medium-Sized Rings","volume":"55","author":"Yet","year":"1999","journal-title":"Tetrahedron"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1021\/ar960101v","article-title":"Diverse Methods for Medium Ring Synthesis","volume":"31","author":"Molander","year":"1998","journal-title":"Acc. Chem. Res."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1011","DOI":"10.3987\/REV-07-612","article-title":"Advances in the Synthesis and Biological Perspectives of Benzannulated Medium Ring Heterocycles","volume":"71","author":"Majhi","year":"2007","journal-title":"Heterocycles"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"8780","DOI":"10.1002\/chem.201700467","article-title":"Ring-Expansion Reactions in the Synthesis of Macrocycles and Medium-Sized Rings","volume":"23","author":"Donald","year":"2017","journal-title":"Chem. Eur. J."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2963","DOI":"10.1021\/cr990407q","article-title":"Metal-Mediated Synthesis of Medium-Sized Rings","volume":"100","author":"Yet","year":"2000","journal-title":"Chem. Rev."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1007\/s13738-014-0451-5","article-title":"Metal catalysts: Applications in higher-membered N-heterocycles synthesis","volume":"12","author":"Kaur","year":"2015","journal-title":"J. Iran. Chem. Soc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"731","DOI":"10.2174\/138527209788167213","article-title":"New Synthetic Strategies for Medium-Sized and Macrocyclic Compounds by Palladium-Catalyzed Cyclization","volume":"13","author":"Majumdar","year":"2009","journal-title":"Curr. Org. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1152","DOI":"10.1039\/c1ra00494h","article-title":"Regioselective formation of medium-ring heterocycles of biological relevance by intramolecular cyclization","volume":"1","author":"Majumdar","year":"2011","journal-title":"RSC Adv."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1623","DOI":"10.1039\/C1CC15238F","article-title":"Microwave-assisted synthesis of medium-sized heterocycles","volume":"48","author":"Sharma","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"6345","DOI":"10.1021\/ja00128a025","article-title":"Palladium-Catalyzed Cyclization of Haloallenes. A New General Route to Common, Medium, and Large Ring Compounds via Cyclic Carbopalladation","volume":"117","author":"Ma","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"3593","DOI":"10.1055\/s-0029-1216984","article-title":"Palladium(0)-Catalyzed Intramolecular Heck Reaction: A Resourceful Route for the Synthesis of Naphthoxepine and Naphthoxocine Derivatives","volume":"2009","author":"Majumdar","year":"2009","journal-title":"Synthesis"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3857","DOI":"10.1055\/s-0028-1083228","article-title":"Novel Synthesis of Oxathiocine Derivatives by Wittig Olefination and Intramolecular Heck Reaction via an 8-endo-trig Cyclization","volume":"2008","author":"Majumdar","year":"2008","journal-title":"Synthesis"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"669","DOI":"10.1016\/j.tet.2014.12.016","article-title":"Palladium catalyzed intramolecular cascade type cyclizations: Interesting Approach towards naphthoquinone derivatives having an O-containing heterocyclic skeleton","volume":"71","author":"Nandi","year":"2015","journal-title":"Tetrahedron"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"979","DOI":"10.1055\/s-2008-1072510","article-title":"Novel Synthesis of Nine-Membered Oxa-Heterocycles by Pd(0)-Catalyzed Intramolecular Heck Reaction via Unusual 9-endo-trig-Mode Cyclization","volume":"2008","author":"Majumdar","year":"2008","journal-title":"Synlett"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"3005","DOI":"10.1021\/ol0487884","article-title":"Synthesis of Medium Ring Heterocycles Using an Intramolecular Heck Reaction","volume":"6","author":"Arnold","year":"2004","journal-title":"Org. Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"5517","DOI":"10.1016\/j.tet.2013.04.090","article-title":"Design and synthesis of carbohydrate based medium sized sulfur containing benzannulated macrocycles: Applications of Sonogashira and Heck coupling","volume":"69","author":"Hussain","year":"2013","journal-title":"Tetrahedron"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1287","DOI":"10.1039\/C39840001287","article-title":"Palladium-catalysed vinylation of organic halides under solid\u2013liquid phase transfer conditions","volume":"19","author":"Jeffery","year":"1984","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"ref_27","first-page":"447","article-title":"Synthesis of conformationally constrained phenylalanine analogues via 7-, 8- and 9-endo Heck cyclisations","volume":"1","author":"Guillo","year":"1997","journal-title":"J. Chem. Soc. Perkin Trans. 1"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"4223","DOI":"10.1021\/ol7018357","article-title":"Applications of Multicomponent Reactions for the Synthesis of Diverse Heterocyclic Scaffolds","volume":"9","author":"Sunderhaus","year":"2007","journal-title":"Org. Lett."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1315","DOI":"10.1055\/s-0029-1219276","article-title":"Concise Synthesis of Pyrimido-azocine Derivatives via Aza-Claisen Rearrangement and Intramolecular Heck Reaction","volume":"2010","author":"Majumdar","year":"2010","journal-title":"Synthesis"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"5207","DOI":"10.1021\/ol052033v","article-title":"Concise synthesis of (\u00b1)-rhazinilam through direct coupling","volume":"7","author":"Bowie","year":"2005","journal-title":"Org. Lett."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"4501","DOI":"10.1039\/c2cc31358h","article-title":"A cascade reaction of pyrrole-2-carbaldehyde substituted Morita\u2013Baylis\u2013Hillman adducts in the presence of tetrabutylammonium hydroxide or acetate to construct aza-heterocycles","volume":"48","author":"Huang","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1575","DOI":"10.1039\/C3CS60369E","article-title":"Synthesis of heterocycles via transition-metal- catalyzed hydroarylation of alkynes","volume":"43","author":"Yamamoto","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"16718","DOI":"10.1002\/chem.201603044","article-title":"Carbopalladation Cascades Using Carbon\u2013Carbon Triple Bonds: Recent Advances to Access Complex Scaffolds","volume":"22","author":"Werz","year":"2016","journal-title":"Chem. Eur. J."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1767","DOI":"10.1055\/s-0036-1588708","article-title":"Cyclocarbopalladation as a Key Step in Cascade Reactions: Recent Developments","volume":"49","author":"Blouin","year":"2017","journal-title":"Synthesis"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3017","DOI":"10.1021\/ol071079g","article-title":"Efficient Synthesis of the 3-Benzazepine Framework via Intramolecular Heck Reductive Cyclization","volume":"9","author":"Donets","year":"2007","journal-title":"Org. Lett."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1837","DOI":"10.1002\/ejoc.201001669","article-title":"Synthesis of the Azocino[cd]indole Framework through Pd-Catalyzed Intramolecular Acetylene Hydroarylation","volume":"2011","author":"Peshkov","year":"2011","journal-title":"Eur. J. Org. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"3372","DOI":"10.1016\/j.tetlet.2010.04.084","article-title":"Palladium-mediated reductive Mizoroki\u2013Heck cyclization strategy for the regioselective formation of dibenzoazocinone framework","volume":"51","author":"Majumdar","year":"2010","journal-title":"Tet. Lett."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"3187","DOI":"10.1002\/adsc.201200703","article-title":"Reductive Cyclization of Bromoenynamides with Alcohols as Hydride Source: Synthesis and Reactions of 2-Amidodienes","volume":"354","author":"Greenaway","year":"2012","journal-title":"Adv. Synth. Catal."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"3060","DOI":"10.1021\/ol501165h","article-title":"Cyclocarbopalladation\/Cross-Coupling Cascade Reactions in Sulfide Series: Access to Sulfur Heterocycles","volume":"16","author":"Castanheiro","year":"2014","journal-title":"Org. Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"624","DOI":"10.1016\/j.crci.2016.12.007","article-title":"Comparative study on the reactivity of propargyl and alkynylsulfides in palladium-catalyzed domino reactions","volume":"20","author":"Castanheiro","year":"2017","journal-title":"Comptes Rendus Chim."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"4505","DOI":"10.1021\/acs.joc.8b00213","article-title":"Synthesis of Sulfur-Containing Exo-Bicyclic Dienes and Their Diels\u2014Alder Reactions to Access Thiacycle-Fused Polycyclic Systems","volume":"83","author":"Castanheiro","year":"2018","journal-title":"J. Org. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1361","DOI":"10.1002\/ejoc.201801686","article-title":"Synthesis of Benzimidazole-Fused Medium-Sized N,S-Heterocycles via Palladium-Catalyzed Cyclizations","volume":"2019","author":"Wagner","year":"2019","journal-title":"Eur. J. Org. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"5943","DOI":"10.1021\/acs.orglett.9b02067","article-title":"Tandem Double-Cross-Coupling\/Hydrothiolation Reaction of 2-Sulfenyl Benzimidazoles with Boronic Acids","volume":"21","author":"Choury","year":"2019","journal-title":"Org. Lett."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"8613","DOI":"10.1016\/S0040-4020(02)00763-9","article-title":"Palladium catalysed queuing processes. Part 4: Termolecular cyclisation\u2013anion capture cascades employing allene as a relay switch and secondary amines as nucleophiles","volume":"58","author":"Grigg","year":"2002","journal-title":"Tetrahedron"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"12564","DOI":"10.1021\/acs.chemrev.6b00512","article-title":"Applications of Palladium-Catalyzed C\u2013N Cross-Coupling Reactions","volume":"116","author":"Buchwald","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"9283","DOI":"10.1039\/c3cs60228a","article-title":"C\u2013N bond forming cross-coupling reactions: An overview","volume":"42","author":"Bariwal","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"4774","DOI":"10.1002\/anie.200351923","article-title":"One-Pot Synthesis of Polyheterocycles by a Palladium-Catalyzed Intramolecular N-Arylation\/ C-H Activation\/Aryl\u2013Aryl Bond-Forming Domino Process","volume":"42","author":"Cuny","year":"2003","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"3291","DOI":"10.1021\/jo052420i","article-title":"Palladium-Mediated Intramolecular Aryl Amination on Furanose Derivatives: An Expedient Approach to the Synthesis of Chiral Benzoxazocine Derivatives and Tricyclic Nucleosides","volume":"71","author":"Neogi","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"7727","DOI":"10.1021\/jo4013767","article-title":"Synthesis of (\u2212)-Epi-Indolactam V by an Intramolecular Buchwald\u2013Hartwig C\u2013N Coupling Cyclization Reaction","volume":"78","author":"Mari","year":"2013","journal-title":"J. Org. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"7376","DOI":"10.1002\/chem.200900477","article-title":"Solvent-Enhanced Diastereo- and Regioselectivity in the PdII-Catalyzed Synthesis of Six- and Eight-Membered Heterocycles via cis-Aminopalladation","volume":"15","author":"Szakonyi","year":"2009","journal-title":"Chem. Eur. J."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"8744","DOI":"10.1021\/ja048693x","article-title":"Palladium(0)-Catalyzed Synthesis of Medium-Sized Heterocycles by Using Bromoallenes as an Allyl Dication Equivalent","volume":"126","author":"Ohno","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"6859","DOI":"10.1021\/jo980516p","article-title":"Synthesis of Medium-Ring Nitrogen Heterocycles via Palladium-Catalyzed Heteroannulation of 1,2-Dienes","volume":"63","author":"Larock","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"14776","DOI":"10.1021\/ja053650h","article-title":"Intramolecular Carbonylation Reactions with Recyclable Palladium-Complexed Dendrimers on Silica: Synthesis of Oxygen, Nitrogen, or Sulfur-Containing Medium Ring Fused Heterocycles","volume":"127","author":"Lu","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"2200","DOI":"10.1002\/chem.201405181","article-title":"A Versatile Synthesis of -Lactam-Fused Oxacycles through the Palladium-Catalyzed Chemo-, Regio-, and Diastereoselective Cyclization of Allenic Diols","volume":"21","author":"Alcaide","year":"2015","journal-title":"Chem. Eur. J."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1912","DOI":"10.1039\/C9SC04569D","article-title":"From 1,2-difunctionalisation to cyanide-transfer cascades\u2013Pd-catalysed cyanosulfenylation of internal (oligo)alkynes","volume":"11","author":"Loch","year":"2020","journal-title":"Chem. Sci."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"2927","DOI":"10.1002\/anie.201611474","article-title":"Construction of Nine-Membered Heterocycles through Palladium- Catalyzed Formal [5+4] Cycloaddition","volume":"56","author":"Yang","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"15304","DOI":"10.1021\/jacs.7b09161","article-title":"Nine-Membered Benzofuran-Fused Heterocycles: Enantioselective Synthesis by Pd-Catalysis and Rearrangement via Transannular Bond Formation","volume":"139","author":"Rong","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"652","DOI":"10.1002\/adsc.201701247","article-title":"Formal [5 + 3] Cycloaddition of Zwitterionic Allylpalladium Intermediates with Azomethine Imines for Construction of N,O- Containing Eight-Membered Heterocycles","volume":"360","author":"Yuan","year":"2018","journal-title":"Adv. Synth. Catal."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"836","DOI":"10.1002\/adsc.201801359","article-title":"Palladium-Catalyzed Propargylic [n + 2] Cycloaddition: An Efficient Strategy for Construction of Benzo-Fused Medium-Sized Heterocycles","volume":"361","author":"Liu","year":"2019","journal-title":"Adv. Synth. Catal."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"3525","DOI":"10.1039\/C3CS60289C","article-title":"Copper catalysed Ullmann type chemistry: From mechanistic aspects to modern development","volume":"43","author":"Sambiagio","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"ref_61","doi-asserted-by":"crossref","unstructured":"Evano, G. (2014). Blanchard, N. Copper-Mediated Cross-Coupling Reactions, John Wiley & Sons.","DOI":"10.1002\/9781118690659"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"16136","DOI":"10.1002\/anie.201701690","article-title":"Selected Copper-Based Reactions for C-N, C-O, C-S, and C-C Bond Formation","volume":"56","author":"Bhunia","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1039\/c0sc00107d","article-title":"Diamine ligands in copper-catalyzed reactions","volume":"1","author":"Surry","year":"2010","journal-title":"Chem. Sci."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"5656","DOI":"10.1021\/ja0010507","article-title":"Towards Diversity-Oriented, Stereoselective Syntheses of Biaryl- or Bis(aryl)metal-Containing Medium Rings","volume":"122","author":"Spring","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"310","DOI":"10.1038\/nchem.1878","article-title":"SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes","volume":"6","author":"Vo","year":"2014","journal-title":"Nat. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"9632","DOI":"10.1002\/anie.201904698","article-title":"Copper-Catalyzed Cascade Cyclization of Indolyl Homopropargyl Amides: Stereospecific Construction of Bridged Aza-[n.2.1] Skeletons","volume":"58","author":"Tan","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2198","DOI":"10.1039\/b927161a","article-title":"Reagent based DOS: A \u201cClick, Click, Cyclize\u201d strategy to probe chemical space","volume":"8","author":"Rolfe","year":"2010","journal-title":"Org. Biomol. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"4781","DOI":"10.1021\/ol052126c","article-title":"Copper-Catalyzed Synthesis of Medium- and Large-Sized Nitrogen Heterocycles via N-Arylation of Phosphoramidates and Carbamates","volume":"7","author":"Yang","year":"2005","journal-title":"Org. Lett."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"2139","DOI":"10.1016\/j.tet.2017.02.061","article-title":"A modular CuI-L-proline catalyzed one-pot route for the rapid access of constrained and privileged hetero-atom-linked medium-sized ring systems","volume":"73","author":"Srinivasulu","year":"2017","journal-title":"Tetrahedron"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"8665","DOI":"10.1021\/jo8016617","article-title":"Copper-Catalyzed Intramolecular N-Vinylation of Sulfonamides: General and Efficient Synthesis of Heterocyclic Enamines and Macrolactams","volume":"73","author":"Lu","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"3407","DOI":"10.1002\/anie.201814331","article-title":"Catalytic Asymmetric Synthesis of \u03b1-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles","volume":"58","author":"Dai","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"2981","DOI":"10.1002\/chem.201002093","article-title":"Novel and Efficient Copper-Catalysed Synthesis of Nitrogen-Linked Medium-Ring Biaryls","volume":"17","author":"Kenwright","year":"2011","journal-title":"Chem. Eur. J."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"5448","DOI":"10.1021\/ol4025259","article-title":"Concise Copper-Catalyzed Synthesis of Tricyclic Biaryl Ether-Linked Aza-Heterocyclic Ring Systems","volume":"15","author":"Mestichelli","year":"2013","journal-title":"Org. Lett."},{"key":"ref_74","doi-asserted-by":"crossref","unstructured":"Bandini, M. (2016). Topics in Heterocyclic Chemistry. Au-Catalyzed Synthesis and Functionalization of Heterocycles, Springer International Publishing.","DOI":"10.1007\/978-3-319-35144-5"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1105","DOI":"10.1002\/anie.200503484","article-title":"Gold-Catalyzed Intramolecular Reaction of Indoles with Alkynes: Facile Formation of Eight-Membered Rings and an Unexpected Allenylation","volume":"45","author":"Ferrer","year":"2006","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"1358","DOI":"10.1002\/chem.200601324","article-title":"Intra- and Intermolecular Reactions of Indoles with Alkynes Catalyzed by Gold","volume":"13","author":"Ferrer","year":"2007","journal-title":"Chem. Eur. J."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"9015","DOI":"10.1016\/j.tet.2009.08.067","article-title":"Synthesis of the Tetracyclic Core Skeleton of the Lundurines by a Gold-Catalyzed Cyclization","volume":"65","author":"Ferrer","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"2841","DOI":"10.1002\/adsc.201200305","article-title":"Synthesis of Azocino[5,4- b ]Indoles via Gold-Catalyzed Intramolecular Alkyne Hydroarylation","volume":"354","author":"Peshkov","year":"2012","journal-title":"Adv. Synth. Catal."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"2543","DOI":"10.1021\/acs.joc.9b03256","article-title":"Gold(I)-Catalyzed Cascade Cyclization of Anilines with Diynes: Controllable Formation of Eight-Membered Ring-Fused Indoles and Propellane-Type Indolines","volume":"85","author":"Yamaguchi","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1225","DOI":"10.1039\/C7CC09250D","article-title":"Synthesis of Indolizine Derivatives Containing Eight-Membered Rings via a Gold-Catalyzed Two-Fold Hydroarylation of Diynes","volume":"54","author":"Liu","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"13937","DOI":"10.1039\/C5CC05808B","article-title":"A Gold-Catalyzed 1,2-Acyloxy Migration\/Intramolecular Cyclopropanation\/Ring Enlargement Cascade: Syntheses of Medium-Sized Heterocycles","volume":"51","author":"Sun","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"5519","DOI":"10.1039\/C5SC01806D","article-title":"Gold(I)-Catalyzed Cycloisomerization of Vinylidenecyclopropane-Enes via Carbene or Non-Carbene Processes","volume":"6","author":"Li","year":"2015","journal-title":"Chem. Sci."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"9076","DOI":"10.1002\/anie.201103832","article-title":"Gold(I)-Catalyzed Synthesis of Benzoxocines by an 8-Endo-Dig Cyclization","volume":"50","author":"Wittstein","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"10789","DOI":"10.1002\/anie.201406486","article-title":"Gold-Catalyzed 1,2-Acyloxy Migration\/Intramolecular [3+2] 1,3-Dipolar Cycloaddtion Cascade Reaction: An Efficient Strategy for Syntheses of Medium-Sized-Ring Ethers and Amines","volume":"53","author":"Zhao","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"4484","DOI":"10.1016\/j.tetlet.2014.06.060","article-title":"Silver(I) and Gold(I)-Promoted Synthesis of Alkylidene Lactones and 2H-Chromenes from Salicylic and Anthranilic Acid Derivatives","volume":"55","author":"Porcel","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"418","DOI":"10.1021\/ol503273v","article-title":"Synthesis of Oxazocenones via Gold(I)-Catalyzed 8- Endo -Dig Hydroalkoxylation of Alkynamides","volume":"17","author":"Scully","year":"2015","journal-title":"Org. Lett."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"698","DOI":"10.1021\/ml200120m","article-title":"Synthesis of a Novel Suppressor of \u03b2-Cell Apoptosis via Diversity-Oriented Synthesis","volume":"2","author":"Chou","year":"2011","journal-title":"ACS Med. Chem. Lett."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"4125","DOI":"10.1021\/jm400397x","article-title":"Small-Molecule Inhibitors of Cytokine-Mediated STAT1 Signal Transduction in \u03b2-Cells with Improved Aqueous Solubility","volume":"56","author":"Scully","year":"2013","journal-title":"Med. Chem."},{"key":"ref_89","doi-asserted-by":"crossref","unstructured":"Kong, X., Guo, X.-Y., Gu, Z.-Y., Wei, L.-S., Liu, L.-L., Mo, D.-L., Pan, C., and Su, G.-F. (2020). Silver(I)-Catalyzed Selective Hydroalkoxylation of C2-Alkynyl Quinazolinones to Synthesize Quinazolinone-Fused Eight-Membered N.,O-Heterocycles. Org. Chem. Front.","DOI":"10.1039\/D0QO00437E"},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"7862","DOI":"10.1002\/anie.201502256","article-title":"Gold-Catalyzed Cascade Cyclization of 2-Alkynyl- N -Propargylanilines by Rearrangement of a Propargyl Group","volume":"54","author":"Tokimizu","year":"2015","journal-title":"Angew. Chem. Int. Ed."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/14\/3147\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T09:49:33Z","timestamp":1760176173000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/14\/3147"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,7,9]]},"references-count":90,"journal-issue":{"issue":"14","published-online":{"date-parts":[[2020,7]]}},"alternative-id":["molecules25143147"],"URL":"https:\/\/doi.org\/10.3390\/molecules25143147","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,7,9]]}}}