{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T09:13:08Z","timestamp":1788513188706,"version":"build-2803163510"},"reference-count":52,"publisher":"American Chemical Society (ACS)","issue":"4","license":[{"start":{"date-parts":[[2019,4,9]],"date-time":"2019-04-09T00:00:00Z","timestamp":1554768000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/100001309","name":"Research Corporation for Science Advancement","doi-asserted-by":"publisher","award":["23248"],"award-info":[{"award-number":["23248"]}],"id":[{"id":"10.13039\/100001309","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009842","name":"University of West Florida","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100009842","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2019,4,30]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The synthesis of 2,3-disubstituted benzo[b]thiophenes with selective placement of a chlorine moiety at the 3 position while maintaining diversity at the 2 position has only been accomplished by a handful of conditions in the past. The development of a greener, less expensive, and simpler method is paramount for the exploration of innovative compounds for application in medicinal and materials chemistry. Herein, the first reported copper-catalyzed electrophilic chlorocyclization method was developed and employed across diverse substrates to generate highly functionalized 2,3-disubstituted benzo[b]thiophenes and 2,3,5-trisubstituted thiophenes in very high yields. This method was optimized in both ethanol and acetonitrile in a comparative solvent study. The utility of this method was further expanded beyond chlorocyclization by changing the sodium halide to generate bromo- and iodocyclization products in excellent yields.<\/jats:p>","DOI":"10.1021\/acsomega.9b00300","type":"journal-article","created":{"date-parts":[[2019,4,9]],"date-time":"2019-04-09T15:59:05Z","timestamp":1554825545000},"page":"6538-6545","source":"Crossref","is-referenced-by-count":16,"title":["Copper-Catalyzed Electrophilic Chlorocyclization Reaction\nUsing Sodium Chloride as the Source of Electrophilic Chlorine"],"prefix":"10.1021","volume":"4","author":[{"given":"Christopher","family":"Walter","sequence":"first","affiliation":[{"name":"University of West Florida , , , ,","place":["Pensacola, Florida, United States, 32514"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Natalie","family":"Fallows","sequence":"additional","affiliation":[{"name":"University of West Florida , , , ,","place":["Pensacola, Florida, United States, 32514"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8193-0004","authenticated-orcid":true,"given":"Tanay","family":"Kesharwani","sequence":"additional","affiliation":[{"name":"University of West Florida , , , ,","place":["Pensacola, Florida, United States, 32514"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2019,4,9]]},"reference":[{"key":"2026090322114165900_cit1","doi-asserted-by":"publisher","first-page":"D668","DOI":"10.1093\/nar\/gkj067","article-title":"DrugBank:\na comprehensive resource for in silico drug discovery and exploration","volume":"34","author":"Wishart","year":"2006","journal-title":"Nucleic Acids Res."},{"key":"2026090322114165900_cit2","doi-asserted-by":"publisher","first-page":"303","DOI":"10.2174\/138945010790711996","article-title":"Halogen\nAtoms in the Modern Medicinal\nChemistry: Hints for the Drug Design","volume":"11","author":"Hernandes","year":"2010","journal-title":"Curr.\nDrug Targets"},{"key":"2026090322114165900_cit3a","doi-asserted-by":"publisher","first-page":"5474","DOI":"10.1021\/ol102350v","article-title":"Gold(III)-Catalyzed Halogenation\nof Aromatic Boronates with N-Halosuccinimides","volume":"12","author":"Qiu","year":"2010","journal-title":"Org. 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Methodology and Regioselective\nSynthesis of Useful Contiguously 3- and 6-Substituted 2-Methoxybenzoic\nAcid Building Blocks","volume":"8","author":"Nguyen","year":"2006","journal-title":"Org. Lett."},{"key":"2026090322114165900_cit5f","doi-asserted-by":"publisher","first-page":"3781","DOI":"10.1021\/jo00117a033","article-title":"Diazines 13:\nMetalation without ortho-Directing Group-Functionalization\nof Diazines via Direct Metalation","volume":"60","author":"Ple","year":"1995","journal-title":"J. Org. Chem."},{"key":"2026090322114165900_cit5g","doi-asserted-by":"publisher","first-page":"2101","DOI":"10.1021\/jo00132a022","article-title":"Regioselective Metalation Reactions of Some Substituted\n(Methoxymethoxy)arenes","volume":"47","author":"Winkle","year":"1982","journal-title":"J. Org. 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Med.\nChem."},{"key":"2026090322114165900_cit7c","doi-asserted-by":"publisher","first-page":"4872","DOI":"10.1016\/j.bmcl.2005.04.078","article-title":"Carbonic\nAnhydrase Inhibitors: Inhibition of Cytosolic\/Tumor-Associated Carbonic\nAnhydrase Isozymes I, II, and IX with Benzo[b]thiophene\n1,1-Dioxide Sulfonamides","volume":"15","author":"Innocenti","year":"2005","journal-title":"Bioorg. Med. Chem.\nLett."},{"key":"2026090322114165900_cit7d","doi-asserted-by":"publisher","first-page":"2346","DOI":"10.1021\/jm049541f","article-title":"Novel Cyano-\nand N-Isopropylamidino-Substituted Derivatives of\nBenzo[b]Thiophene-2-Carboxanilides and Benzo[b]Thieno[2,3-c] Quinolones: Synthesis,\nPhotochemical Synthesis, Crystal Structure Determination, and Antitumor\nEvaluation","volume":"48","author":"Jarak","year":"2005","journal-title":"J. Med. 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Chem."},{"key":"2026090322114165900_cit15","doi-asserted-by":"publisher","first-page":"4704","DOI":"10.1021\/jo500377v","article-title":"Transition\nMetal-Catalyzed Cascade\nCyclization of Aryldiynes to Halogenated Benzo[b]Naphtho[2,1-d]Thiophene Derivatives","volume":"79","author":"Chen","year":"2014","journal-title":"J. Org. 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Med. Chem."},{"key":"2026090322114165900_cit21","doi-asserted-by":"publisher","first-page":"1905","DOI":"10.1021\/jo011016q","article-title":"Synthesis of 2,3-Disubstituted\nBenzo[b]thiophenes via Palladium-Catalyzed Coupling\nand Electrophilic Cyclization\nof Terminal Acetylenes","volume":"67","author":"Yue","year":"2002","journal-title":"J. Org. 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