{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T01:01:46Z","timestamp":1788915706049,"version":"build-2803163510"},"reference-count":51,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2023,5,26]],"date-time":"2023-05-26T00:00:00Z","timestamp":1685059200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22171173"],"award-info":[{"award-number":["22171173"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["B14041"],"award-info":[{"award-number":["B14041"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["2017SF-064"],"award-info":[{"award-number":["2017SF-064"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"111 Project","award":["22171173"],"award-info":[{"award-number":["22171173"]}]},{"name":"111 Project","award":["B14041"],"award-info":[{"award-number":["B14041"]}]},{"name":"111 Project","award":["2017SF-064"],"award-info":[{"award-number":["2017SF-064"]}]},{"name":"Key Research and Development Project of Shaanxi Science and Technology Department","award":["22171173"],"award-info":[{"award-number":["22171173"]}]},{"name":"Key Research and Development Project of Shaanxi Science and Technology Department","award":["B14041"],"award-info":[{"award-number":["B14041"]}]},{"name":"Key Research and Development Project of Shaanxi Science and Technology Department","award":["2017SF-064"],"award-info":[{"award-number":["2017SF-064"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The palladium-catalyzed Sonogashira coupling of \u03b1, \u03b2-unsaturated acid derivatives offers a diversity-oriented synthetic strategy for cross-conjugated enynones. However, the susceptibility of the unsaturated C-C bonds adjacent to the carbonyl group toward Pd catalysts makes the direct conversion of \u03b1, \u03b2-unsaturated derivatives as acyl electrophiles to cross-conjugated ketones rare. This work presents a highly selective C-O activation approach to prepare cross-conjugated enynones using \u03b1, \u03b2-unsaturated triazine esters as acyl electrophiles. Under base and phosphine ligand-free conditions, NHC-Pd(II)-Allyl precatalyst alone catalyzed the cross-coupling of \u03b1, \u03b2-unsaturated triazine esters with terminal alkynes efficiently, yielding 31 cross-conjugated enynones with diverse functional groups. This method demonstrates the potential of triazine-mediated C-O activation for preparing highly functionalized ketones.<\/jats:p>","DOI":"10.3390\/molecules28114364","type":"journal-article","created":{"date-parts":[[2023,5,27]],"date-time":"2023-05-27T16:17:33Z","timestamp":1685204253000},"page":"4364","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["A General Synthesis of Cross-Conjugated Enynones through Pd Catalyzed Sonogashira Coupling with Triazine Esters"],"prefix":"10.3390","volume":"28","author":[{"given":"Dezhi","family":"Lin","sequence":"first","affiliation":[{"name":"Key Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi\u2019an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi\u2019an 710119, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yunfang","family":"Liu","sequence":"additional","affiliation":[{"name":"South China Institute of Environmental Science, Ministry of Ecology and Environment, Guangzhou 510655, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hongyu","family":"Yang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi\u2019an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi\u2019an 710119, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4310-4649","authenticated-orcid":false,"given":"Xiao","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi\u2019an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi\u2019an 710119, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huaming","family":"Sun","sequence":"additional","affiliation":[{"name":"Key Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi\u2019an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi\u2019an 710119, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yajun","family":"Jian","sequence":"additional","affiliation":[{"name":"Key Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi\u2019an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi\u2019an 710119, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8810-9606","authenticated-orcid":false,"given":"Weiqiang","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi\u2019an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi\u2019an 710119, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jianming","family":"Yang","sequence":"additional","affiliation":[{"name":"Xi\u2019an Modern Chemistry Research Institute, Xi\u2019an 710065, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ziwei","family":"Gao","sequence":"additional","affiliation":[{"name":"Key Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi\u2019an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi\u2019an 710119, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,5,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"7447","DOI":"10.1002\/anie.200502313","article-title":"Complexation-Initiated Intramolemlar 4+2 Cycloaddition: Construction of Bridged-Type Cycloadducts","volume":"44","author":"Iwasawa","year":"2005","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"2532","DOI":"10.1021\/ja910696x","article-title":"A Metal-Catalyzed Intermolecular 5+2 Cycloaddition\/Nazarov Cyclization Sequence and Cascade","volume":"132","author":"Wender","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"6891","DOI":"10.1039\/c1cc11758k","article-title":"A Domino Pericyclic Route to Polysubstituted Salicylic Acid Derivatives: Four Sequential Processes from Enynones and Ketene Silyl Acetals","volume":"47","author":"Hamura","year":"2011","journal-title":"Chem. Commun."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"4327","DOI":"10.1021\/acs.orglett.7b01996","article-title":"Cascade C=O\/C=C\/C\u2013N Bond Formation: Metal-Free Reactions of 1,4-Diynes and 1-En-4-Yn-3-Ones with Isoquinoline and Quinoline N-Oxides","volume":"19","author":"Zhang","year":"2017","journal-title":"Org. Lett."},{"key":"ref_5","first-page":"431","article-title":"Synthesis, Double Michael-Reaction and Antimicrobial Activity of Cross-Conjugated Enyone","volume":"35","author":"Rele","year":"1996","journal-title":"Ind. J. Chem. Sect. B"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2469","DOI":"10.1021\/ol800754w","article-title":"One-Pot Syntheses of 2,3-Dihydrothiopyran-4-one Derivatives by Pd\/Cu-Catalyzed Reactions of \u03b1,\u03b2-Unsaturated Thioesters with Propargyl Alcohols","volume":"10","author":"Minami","year":"2008","journal-title":"Org. Lett."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"3635","DOI":"10.1002\/ejoc.201700423","article-title":"Br\u00f8nsted Acid Promoted Cyclization of Cross-Conjugated Enynones into Dihydropyran-4-ones","volume":"2017","author":"Saulnier","year":"2017","journal-title":"Eur. J. Org. Chem."},{"key":"ref_8","first-page":"773","article-title":"Acetylenic Aquatic Anticancer Agents and Related Compounds","volume":"1","author":"Dembitsky","year":"2006","journal-title":"Nat. Prod. Commun."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1842","DOI":"10.1080\/14786419.2012.763128","article-title":"Petroacetylene, a new polyacetylene from the Marine Sponge Petrosiasolida that Inhibits Blastulation of Starfish Embryos","volume":"27","author":"Ohta","year":"2013","journal-title":"Nat. Prod. Res."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"8169","DOI":"10.1021\/acs.orglett.1c02848","article-title":"One-Pot Synthesis of Symmetrical and Asymmetrical 3-Amino Diynes via Cu(I)-Catalyzed Reaction of Enaminones with Terminal Alkynes","volume":"23","author":"Zhang","year":"2021","journal-title":"Org. Lett."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1339","DOI":"10.1021\/jo026481h","article-title":"Synthesis of Unsymmetrically Substituted 1,3-Butadiynes and 1,3,5-Hexatriynes via Alkylidene Carbenoid Rearrangements","volume":"68","author":"Shun","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1149","DOI":"10.1002\/adsc.201300018","article-title":"Double Gold-Catalysed Annulation of Indoles by Enynones","volume":"355","author":"Heffernan","year":"2013","journal-title":"Adv. Synth. Catal."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"516","DOI":"10.1021\/ol203114a","article-title":"Catalytic Diastereoselective Reduction of \u03b1,\u03b2-Epoxy and \u03b1,\u03b2-Aziridinyl Ynones","volume":"14","author":"Druais","year":"2012","journal-title":"Org. Lett."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2077","DOI":"10.1002\/adsc.201300265","article-title":"Gold(III) Chloride-Catalyzed 6-endo-trig Oxa-Michael Addition Reactions for Diastereoselective Synthesis of Fused Tetrahydropyranones","volume":"355","author":"Ciesielski","year":"2013","journal-title":"Adv. Synth. Catal."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"20605","DOI":"10.1021\/ja310482z","article-title":"Ivorenolide A, an Unprecedented Immunosuppressive Macrolide from Khaya ivorensis: Structural Elucidation and Bioinspired Total Synthesis","volume":"134","author":"Zhang","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"4698","DOI":"10.1021\/acs.orglett.5b02152","article-title":"Selective Access to 4-Substituted 2-Aminothiazoles and 4-Substituted 5-Thiocyano-2-aminothiazoles from Vinyl Azides and Potassium Thiocyanate Switched by Palladium and Iron Catalysts","volume":"17","author":"Chen","year":"2012","journal-title":"Org. Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"4986","DOI":"10.1039\/c1cs15109f","article-title":"Palladium-Catalyzed Carbonylative Coupling Reactions between Ar\u2013X and Carbon Nucleophiles","volume":"40","author":"Wu","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"146","DOI":"10.3184\/030823401103169306","article-title":"A Convenient Synthesis of Conjugated Acetylenicketones by Copper(I)-Catalysis under Microwaveirradiation","volume":"4","author":"Wang","year":"2001","journal-title":"J. Chem. Res."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1613","DOI":"10.1021\/jo01324a006","article-title":"Mild, Selective, General Method of Ketone Synthesis from Acid Chlorides and Organotin Compounds Catalyzed by Palladium","volume":"44","author":"Milstein","year":"1979","journal-title":"J. Org. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"777","DOI":"10.1055\/s-1977-24574","article-title":"A Convenient Synthesis of 1-Alkynyl Ketones and 2-Alkynamides","volume":"1977","author":"Tohda","year":"1977","journal-title":"Synthesis"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3151","DOI":"10.1021\/ol048789w","article-title":"A Remarkably Efficient Coupling of Acid Chlorides with Alkynes in Water","volume":"6","author":"Chen","year":"2004","journal-title":"Org. Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1660","DOI":"10.1038\/nprot.2008.152","article-title":"Catalytic Alkynone Generation by Sonogashira Reaction and its Application in Three-Component Pyrimidine Synthesis","volume":"3","year":"2008","journal-title":"Nat. Protoc."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"4936","DOI":"10.1021\/ol1022036","article-title":"One-Pot Three-Step Synthesis of 1,2,3-Triazoles by Copper-Catalyzed Cycloaddition of Azides with Alkynes formed by a Sonogashira Cross-Coupling and Desilylation","volume":"12","author":"Friscourt","year":"2010","journal-title":"Org. Lett."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"10448","DOI":"10.1002\/anie.201103296","article-title":"Catalytic Syntheses of N-Heterocyclic Ynones and Ynediones by In Situ Activation of Carboxylic Acids with Oxalyl Chloride","volume":"50","author":"Boersch","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"12076","DOI":"10.1039\/C6CC06428K","article-title":"Palladium-catalyzed Sonogashira coupling of amides: Access to ynones via C\u2013N bond cleavage","volume":"52","author":"Cui","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1147","DOI":"10.1021\/ol800054b","article-title":"The First Palladium-Catalyzed Desulfitative Sonogashira-Type Cross-Coupling of (Hetero)aryl Thioethers with Terminal Alkynes","volume":"10","author":"Mehta","year":"2008","journal-title":"Org. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3298","DOI":"10.1021\/acs.orglett.5b01466","article-title":"Privilege Ynone Synthesis via Palladium-Catalyzed Alkynylation of \u201cSuper-Active Esters\u201d","volume":"17","author":"Yu","year":"2015","journal-title":"Org. Lett."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"280","DOI":"10.1070\/RCR4808","article-title":"Conjugated Enynones: Preparation, Properties and Applications in Organic Synthesis","volume":"88","author":"Golovanov","year":"2019","journal-title":"Russ. Chem. Rev."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Albano, G., and Aronica, L.A. (2020). Acyl Sonogashira Cross-Coupling: State of the Art and Application to the Synthesis of Heterocyclic Compounds. Catalysts, 10.","DOI":"10.3390\/catal10010025"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2817","DOI":"10.1080\/00397911.2012.745156","article-title":"Pd-Catalyzed Cross-Coupling of Acyl Chlorides with In Situ\u2013Generated Alkynylzinc Derivatives for the Synthesis of Ynones","volume":"43","author":"Yuan","year":"2013","journal-title":"Synth. Commun."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1139\/cjc-2012-0444","article-title":"Pd\/BaSO4-Catalyzed Cross Coupling of Acyl Chlorides with In Situ Generated Alkynylzinc Derivatives for the Synthesis of Ynones","volume":"91","author":"Yuan","year":"2013","journal-title":"Can. J. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1002\/hlca.200890032","article-title":"Copper-Free Sonogashira Coupling of Acid Chlorides with Terminal Alkynes in the Presence of a Reusable Palladium Catalyst: An Improved Synthesis of 3-Iodochromenones (=3-Iodo-4H-1-benzopyran-4-ones)","volume":"91","author":"Likhar","year":"2008","journal-title":"Helv. Chim. Acta"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1002\/chem.200902906","article-title":"Multi-Step Synthesis by Using Modular Flow Reactors: The Preparation of Yne\u2014Ones and Their Use in Heterocycle Synthesis","volume":"16","author":"Baxendale","year":"2010","journal-title":"Chem. Eur. J."},{"key":"ref_34","first-page":"331","article-title":"Synthesis of Ferrocenylethynyl Ketones by Coupling of Ferrocenylethyne with Acyl Chlorides","volume":"3","author":"Yin","year":"2004","journal-title":"Synthesis"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3337","DOI":"10.1081\/SCC-100106045","article-title":"A Facile Synthesis of Conjugated Acetyl Ketones by Pd(II)-Cu(I) Doped KF\/Al2O3-Catalyzed under Microwave Irradiation","volume":"31","author":"Wang","year":"2001","journal-title":"Synth. Commun."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3238","DOI":"10.1039\/c1gc15869d","article-title":"A Supported Palladium Nanocatalyst for Copper Free Acyl Sonogashira Reactions: One-Pot Multicomponent Synthesis of N-Containing Heterocycles","volume":"13","author":"Santra","year":"2011","journal-title":"Green Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1615","DOI":"10.1021\/jo035761+","article-title":"Synthesis of Ynones by Palladium-Catalyzed Acylation of Terminal Alkynes with Acid Chlorides","volume":"69","author":"Alonso","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"9861","DOI":"10.1021\/jo0614801","article-title":"Alkyl, Unsaturated, (Hetero)aryl, and N-Protected \u03b1-Amino Ketones by Acylation of Organometallic Reagents","volume":"71","author":"Katritzky","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"5074","DOI":"10.1039\/C8CC00324F","article-title":"A Robust Multifunctional Ligand-Controlled Palladium-Catalyzed Carbonylation Reaction in Water","volume":"54","author":"Gao","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"13020","DOI":"10.1039\/D1CC05280B","article-title":"Triazine-wingtips Accelerated NHC-Pd Catalysed Carbonylative Sonogashira Cross-Coupling Reaction","volume":"57","author":"Zhang","year":"2021","journal-title":"Chem. Commun."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"7891","DOI":"10.1039\/C8OB01985A","article-title":"Hydroarylation of Unsaturated Carbon\u2013Carbon Bonds in Cross-Conjugated Enynones under the Action of superacid CF3SO3H or Acidic Zeolite HUSY. Reaction Mechanism and DFT Study on Cationic Intermediate Species","volume":"16","author":"Aleksandrova","year":"2018","journal-title":"Org. Biomol. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"15901","DOI":"10.1021\/jacs.9b07037","article-title":"Activating Pyrimidines by Pre-Distortion for the General Synthesis of 7-Aza-indazoles from 2-Hydrazonylpyrimidines via Intramolecular Diels\u2013Alder Reactions","volume":"141","author":"Chen","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2422","DOI":"10.1002\/adsc.201400176","article-title":"A Sulfur Ylides-Mediated Domino Benzannulation Strategy to Construct Biaryls, Alkenylated and Alkynylated Benzene Derivatives","volume":"356","author":"Gao","year":"2014","journal-title":"Adv. Synth. Catal."},{"key":"ref_44","first-page":"612","article-title":"1,5-Diaryl-1-penten-4-yn-3-ones","volume":"58","author":"Utekhina","year":"1988","journal-title":"Russ. J. Gen. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"4219","DOI":"10.1002\/ejoc.201300220","article-title":"Palladium-Catalyzed Ring-Opening Alkynylation of Cyclopropenones","volume":"2013","author":"Matsuda","year":"2013","journal-title":"Eur. J. Org. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1363","DOI":"10.1039\/C7QO00082K","article-title":"Synthesis of 1,4-Enyne-3-ones via Palladium-Catalyzed Sequential decarboxylation And Carbonylation of Allyl Alkynoates","volume":"4","author":"Li","year":"2017","journal-title":"Org. Chem. Front."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"14723","DOI":"10.1002\/anie.201708037","article-title":"Alkynylation of sp2 C(O)\u2013H Bonds Enabled by Photoredox-Mediated Hydrogen-Atom Transfer","volume":"56","author":"Mukherjee","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"3783","DOI":"10.1002\/anie.201411261","article-title":"Palladium-Catalyzed Regio- and Stereoselective Cross-Addition of Terminal Alkynes to Ynol Ethers and Synthesis of 1,4-Enyn-3-ones","volume":"54","author":"Babu","year":"2015","journal-title":"Angew. Chem. Int. Ed"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"8693","DOI":"10.1039\/D2OB01427K","article-title":"Cyclization of arylhydrazones of cross-conjugated enynones: Synthesis of luminescent styryl-1H-pyrazoles and propenyl-1H-pyrazoles","volume":"20","author":"Itakhunov","year":"2022","journal-title":"Org. Biomol. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"7297","DOI":"10.1039\/D0CC01238F","article-title":"Bifunctional phosphine ligand-enabled gold-catalyzed direct cycloisomerization of alkynyl ketones to 2,5-disubstituted furans","volume":"56","author":"Hu","year":"2020","journal-title":"Chem. Commun."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"5095","DOI":"10.1016\/j.tetlet.2006.05.080","article-title":"Synthesis of unsymmetrically 2,6-disubstituted 2,3-dihydrothiopyran-4-ones","volume":"47","author":"Rosiak","year":"2006","journal-title":"Tetrahedron Lett."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/11\/4364\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T19:42:59Z","timestamp":1760125379000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/11\/4364"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,5,26]]},"references-count":51,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2023,6]]}},"alternative-id":["molecules28114364"],"URL":"https:\/\/doi.org\/10.3390\/molecules28114364","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,5,26]]}}}