{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T15:09:06Z","timestamp":1786979346241,"version":"build-2736575974"},"reference-count":112,"publisher":"Wiley","issue":"61","license":[{"start":{"date-parts":[[2024,10,14]],"date-time":"2024-10-14T00:00:00Z","timestamp":1728864000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["BR 5154\/4-1"],"award-info":[{"award-number":["BR 5154\/4-1"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2024,11,4]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The reaction between aldehydes or ketones and alkynes\u2014the carbonyl\u2010alkyne metathesis\u2014constitutes a very useful strategy for the synthesis of \u03b1,\u03b2\u2010unsaturated carbonyls. We now demonstrate that iodine is a highly efficient catalyst for both the intra\u2010 and intermolecular metathesis reaction in very small concentrations (0.1\u20131\u2005mol\u2009%). Our protocol outperforms other catalytic systems, is operationally very simple, cheap, metal\u2010free, and tolerates a large variety of functional groups (e.\u2009g., \u2212CN, \u2212CO\n                    <jats:sub>2<\/jats:sub>\n                    Me, \u2212Br, \u2212OH) at very low catalyst loadings. We can furthermore show that iodine\u2010catalyzed carbonyl\u2010alkyne metatheses can be combined with other iodine\u2010catalyzed reactions in one\u2010pot procedures to afford larger and more complex molecular structures. Finally, our mechanistic studies indicate that the iodonium ion is the active catalyst under the reaction conditions.\n                  <\/jats:p>","DOI":"10.1002\/chem.202402424","type":"journal-article","created":{"date-parts":[[2024,7,22]],"date-time":"2024-07-22T13:19:56Z","timestamp":1721654396000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Iodine\u2010Catalyzed Carbonyl\u2010Alkyne Metathesis Reactions"],"prefix":"10.1002","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0009-0008-0965-7363","authenticated-orcid":false,"given":"Thiemo","family":"Arndt","sequence":"first","affiliation":[{"name":"Institut f\u00fcr Chemie TU Chemnitz  Stra\u00dfe der Nationen 62 09111 Chemnitz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0950-8858","authenticated-orcid":false,"given":"Martin","family":"Breugst","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Chemie TU Chemnitz  Stra\u00dfe der Nationen 62 09111 Chemnitz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,10,14]]},"reference":[{"key":"e_1_2_9_1_1","unstructured":"\u00a0"},{"key":"e_1_2_9_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c01096"},{"key":"e_1_2_9_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7QO01037K"},{"key":"e_1_2_9_4_1","unstructured":"\u00a0"},{"key":"e_1_2_9_5_2","doi-asserted-by":"publisher","DOI":"10.3390\/catal10091092"},{"key":"e_1_2_9_6_2","doi-asserted-by":"publisher","DOI":"10.2174\/2213347XMTAy0MTAh5"},{"key":"e_1_2_9_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CS00391B"},{"key":"e_1_2_9_8_2","doi-asserted-by":"publisher","DOI":"10.3987\/REV-15-836"},{"key":"e_1_2_9_9_1","unstructured":"\u00a0"},{"key":"e_1_2_9_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01585a048"},{"key":"e_1_2_9_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/recl.19590780906"},{"key":"e_1_2_9_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol800539a"},{"key":"e_1_2_9_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol050838x"},{"key":"e_1_2_9_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c06016"},{"key":"e_1_2_9_15_1","unstructured":"\u00a0"},{"key":"e_1_2_9_16_2","doi-asserted-by":"crossref","unstructured":"J.\u2005J. Koenig M. Breugst inHalogen Bonding in Solution 2021 237\u2013268;","DOI":"10.1002\/9783527825738.ch7"},{"key":"e_1_2_9_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201706136"},{"key":"e_1_2_9_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2010.11.086"},{"key":"e_1_2_9_19_2","first-page":"299","volume":"65","author":"Banerjee A. K.","year":"2006","journal-title":"J Sci Ind Res India"},{"key":"e_1_2_9_20_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-950405"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja02172a015"},{"key":"e_1_2_9_22_1","unstructured":"\u00a0"},{"key":"e_1_2_9_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b00445"},{"key":"e_1_2_9_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b00447"},{"key":"e_1_2_9_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b01083"},{"key":"e_1_2_9_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.202100342"},{"key":"e_1_2_9_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202201279"},{"key":"e_1_2_9_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.8b03769"},{"key":"e_1_2_9_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b03229"},{"key":"e_1_2_9_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c00608"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01311a020"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo2000012"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.9b01481"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00032a005"},{"key":"e_1_2_9_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00749"},{"key":"e_1_2_9_36_1","unstructured":"\u00a0"},{"key":"e_1_2_9_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100723a041"},{"key":"e_1_2_9_38_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1995-5213"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00408a029"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2020.152657"},{"key":"e_1_2_9_41_1","unstructured":"\u00a0"},{"key":"e_1_2_9_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol900142r"},{"key":"e_1_2_9_43_2","doi-asserted-by":"publisher","DOI":"10.1039\/b905954g"},{"key":"e_1_2_9_44_1","unstructured":"\u00a0"},{"key":"e_1_2_9_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201101071"},{"key":"e_1_2_9_46_2","volume-title":"Lewis Basicity and Affinity Scales: Data and Measurement","author":"Laurence C.","year":"2010"},{"key":"e_1_2_9_47_1","unstructured":"\u00a0"},{"key":"e_1_2_9_48_2","doi-asserted-by":"publisher","DOI":"10.1016\/0013-4686(74)85026-7"},{"key":"e_1_2_9_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100395a041"},{"key":"e_1_2_9_50_1","unstructured":"\u00a0"},{"key":"e_1_2_9_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01644a001"},{"key":"e_1_2_9_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198503191"},{"key":"e_1_2_9_53_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02841403"},{"key":"e_1_2_9_54_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3RA08810C"},{"key":"e_1_2_9_55_1","unstructured":"\u00a0"},{"key":"e_1_2_9_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.2c00051"},{"key":"e_1_2_9_57_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-018-0065-0"},{"key":"e_1_2_9_58_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms8512"},{"key":"e_1_2_9_59_1","unstructured":"\u00a0"},{"key":"e_1_2_9_60_2","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC02011H"},{"key":"e_1_2_9_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c01251"},{"key":"e_1_2_9_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.8b00499"},{"key":"e_1_2_9_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b02810"},{"key":"e_1_2_9_64_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob06949k"},{"key":"e_1_2_9_65_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201508983"},{"key":"e_1_2_9_66_1","unstructured":"DFT calculations were performed at the B2LYP\u2212D3BJ\/def2-QZVPP\/SMD(MeOH)\/M06\u20132X\/def2-SVP\/SMD(MeOH) level of theory and the def2-TZVP basis set with the corresponding pseudopotential was used for iodine during the optimizations."},{"key":"e_1_2_9_67_1","unstructured":"\u00a0"},{"key":"e_1_2_9_68_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00167-3"},{"key":"e_1_2_9_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00029a019"},{"key":"e_1_2_9_70_2","author":"Schindler C.","year":"2022","journal-title":"ChemRxiv."},{"key":"e_1_2_9_71_1","unstructured":"\u00a0"},{"key":"e_1_2_9_72_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB02090A"},{"key":"e_1_2_9_73_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2003-37515"},{"key":"e_1_2_9_74_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1493"},{"key":"e_1_2_9_75_1","unstructured":"\u00a0"},{"key":"e_1_2_9_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jctc.9b00143"},{"key":"e_1_2_9_77_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CP06869D"},{"key":"e_1_2_9_78_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202004239"},{"key":"e_1_2_9_79_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-007-0310-x"},{"key":"e_1_2_9_80_1","doi-asserted-by":"publisher","DOI":"10.1039\/b508541a"},{"key":"e_1_2_9_81_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp810292n"},{"key":"e_1_2_9_82_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201803652"},{"key":"e_1_2_9_83_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201200497"},{"key":"e_1_2_9_84_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.2148954"},{"key":"e_1_2_9_85_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21759"},{"key":"e_1_2_9_86_1","unstructured":"\u00a0"},{"key":"e_1_2_9_87_2","doi-asserted-by":"publisher","DOI":"10.1039\/b515623h"},{"key":"e_1_2_9_88_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-007-0250-5"},{"key":"e_1_2_9_89_1","unstructured":"Gaussian 16 Revision C.01; M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone G.\u2005A. Petersson H. Nakatsuji X. Li M. Caricato A.\u2005V. Marenich J. Bloino B.\u2005G. Janesko R. Gomperts B. Mennucci H.\u2005P. Hratchian J.\u2005V. Ortiz A.\u2005F. Izmaylov J.\u2005L. Sonnenberg Williams F. Ding F. Lipparini F. Egidi J. Goings B. Peng A. Petrone T. Henderson D. Ranasinghe V.\u2005G. Zakrzewski J. Gao N. Rega G. Zheng W. Liang M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven K. Throssell J.\u2005A. Montgomery Jr. J.\u2005E. Peralta F. Ogliaro M.\u2005J. Bearpark J.\u2005J. Heyd E.\u2005N. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov T.\u2005A. Keith R. Kobayashi J. Normand K. Raghavachari A.\u2005P. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi J.\u2005M. Millam M. Klene C. Adamo R. Cammi J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma O. Farkas J.\u2005B. Foresman D.\u2005J. Fox Wallingford CT 2016."},{"key":"e_1_2_9_90_1","unstructured":"\u00a0"},{"key":"e_1_2_9_91_2","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1327"},{"key":"e_1_2_9_92_2","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1606"},{"key":"e_1_2_9_93_1","unstructured":"\u00a0"},{"key":"e_1_2_9_94_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200902099"},{"key":"e_1_2_9_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo502745j"},{"key":"e_1_2_9_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b01818"},{"key":"e_1_2_9_97_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3OB41624K"},{"key":"e_1_2_9_98_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2018.10.040"},{"key":"e_1_2_9_99_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201801507"},{"key":"e_1_2_9_100_2","doi-asserted-by":"publisher","DOI":"10.1039\/D3OB00671A"},{"key":"e_1_2_9_101_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2005.03.054"},{"key":"e_1_2_9_102_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA27458G"},{"key":"e_1_2_9_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/om7006425"},{"key":"e_1_2_9_104_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00041"},{"key":"e_1_2_9_105_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2009.02.052"},{"key":"e_1_2_9_106_2","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.201700345"},{"key":"e_1_2_9_107_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcc.9b11667"},{"key":"e_1_2_9_108_2","doi-asserted-by":"publisher","DOI":"10.1007\/s12272-012-0406-2"},{"key":"e_1_2_9_109_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201801300"},{"key":"e_1_2_9_110_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1gc15164a"},{"key":"e_1_2_9_111_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1980-28916"},{"key":"e_1_2_9_112_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo500108a"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202402424","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T11:40:12Z","timestamp":1760269212000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202402424"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,10,14]]},"references-count":112,"journal-issue":{"issue":"61","published-print":{"date-parts":[[2024,11,4]]}},"alternative-id":["10.1002\/chem.202402424"],"URL":"https:\/\/doi.org\/10.1002\/chem.202402424","archive":["Portico"],"relation":{"has-preprint":[{"id-type":"doi","id":"10.26434\/chemrxiv-2024-4l3t8","asserted-by":"object"}]},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,10,14]]},"assertion":[{"value":"2024-06-25","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-10-14","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202402424"}}