{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,30]],"date-time":"2026-10-30T09:51:18Z","timestamp":1793353878734,"version":"4.5.0"},"reference-count":29,"publisher":"American Chemical Society (ACS)","issue":"43","license":[{"start":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T00:00:00Z","timestamp":1792022400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T00:00:00Z","timestamp":1792022400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T00:00:00Z","timestamp":1792022400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100012166","name":"National Key Research and Development Program of China","doi-asserted-by":"publisher","award":["2022YFA1504200"],"award-info":[{"award-number":["2022YFA1504200"]}],"id":[{"id":"10.13039\/501100012166","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,30]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>A Lewis base-promoted defluorinative annulation protocol for the preparation of indoline-C2,C3-fused N-heterocyclic scaffolds was described, in which available fluorinated N-arylhydroxylamines, activated alkynes, and ambident N-nucleophiles enabled a modular assembly of diverse indoline-C2,C3-fused N-heterocyclic scaffolds via an interrupted [3,3]-sigmatropic rearrangement of O-alkenyl-N-arylhydroxylamines under mild conditions. This protocol provides a mechanistically distinct and complementary alternative to the established methods for constructing C2,C3-fused indoline architectures.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01446","type":"journal-article","created":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T14:01:18Z","timestamp":1792072878000},"page":"14097-14107","source":"Crossref","is-referenced-by-count":0,"title":["Defluorinative Annulation Triggered by Lewis Base-Promoted\n                    <i>O<\/i>\n                    -Alkenylation\/[3,3]-Sigmatropic Rearrangement of Fluoro-\n                    <i>N<\/i>\n                    -arylhydroxylamines: Synthesis of Fused-Indoline Derivatives"],"prefix":"10.1021","volume":"91","author":[{"given":"Lei","family":"Yang","sequence":"first","affiliation":[{"name":"Jilin University , , 2699 Qianjin Street , ,","place":["Changchun, P. R. China, 130012"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dan-Dan","family":"Wan","sequence":"additional","affiliation":[{"name":"Jilin University , , 2699 Qianjin Street , ,","place":["Changchun, P. R. China, 130012"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Meng-Yu","family":"Liu","sequence":"additional","affiliation":[{"name":"Jilin University , , 2699 Qianjin Street , ,","place":["Changchun, P. R. China, 130012"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9032-0889","authenticated-orcid":true,"given":"Zhong-Lin","family":"Wei","sequence":"additional","affiliation":[{"name":"Jilin University , , 2699 Qianjin Street , ,","place":["Changchun, P. R. China, 130012"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6225-4258","authenticated-orcid":true,"given":"Wei-Wei","family":"Liao","sequence":"additional","affiliation":[{"name":"Jilin University , , 2699 Qianjin Street , ,","place":["Changchun, P. R. China, 130012"]},{"name":"Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , , ,","place":["Shanghai, P. R. China, 200032"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,15]]},"reference":[{"key":"2026103005080185500_cit1a","volume-title":"The Claisen Rearrangement: Methods and Applications","author":"Nubbemeyer","year":"2007","edition":"1"},{"key":"2026103005080185500_cit1b","doi-asserted-by":"publisher","first-page":"3133","DOI":"10.1039\/b901177n","article-title":"[3,3]-Sigmatropic rearrangements: recent applications in the total synthesis of natural products","volume":"38","author":"Ilardi","year":"2009","journal-title":"Chem. Soc. Rev."},{"key":"2026103005080185500_cit1c","doi-asserted-by":"publisher","first-page":"2556","DOI":"10.1002\/anie.201302572","article-title":"Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements","volume":"53","author":"Jones","year":"2014","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026103005080185500_cit1d","doi-asserted-by":"publisher","first-page":"431","DOI":"10.1002\/9781118939901.ch14","volume-title":"Molecular Rearrangements in Organic Synthesis","author":"Anderson","year":"2015"},{"key":"2026103005080185500_cit2a","doi-asserted-by":"publisher","first-page":"447","DOI":"10.1021\/ar200004w","article-title":"Total Synthesis of Indoline Alkaloids: A Cyclopropanation Strategy","volume":"44","author":"Zhang","year":"2011","journal-title":"Acc. Chem. Res."},{"key":"2026103005080185500_cit2b","doi-asserted-by":"publisher","first-page":"702","DOI":"10.1021\/ar5004303","article-title":"Intramolecular Dearomative Oxidative Coupling of Indoles: A Unified Strategy for the Total Synthesis of Indoline Alkaloids","volume":"48","author":"Zi","year":"2015","journal-title":"Acc. Chem. Res."},{"key":"2026103005080185500_cit2c","doi-asserted-by":"publisher","first-page":"2039","DOI":"10.1055\/s-0035-1561638","article-title":"Bioinspired Discovery of Chemical Reactions and Biological Probes","author":"Griffiths","year":"2016","journal-title":"Synlett"},{"key":"2026103005080185500_cit2d","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2019.103436","article-title":"Steering the Antitumor Drug Discovery Campaign towards Structurally Diverse Indolines","volume":"94","author":"Thakur","year":"2020","journal-title":"Bioorg. Chem."},{"key":"2026103005080185500_cit2e","article-title":"Methods of Inhibiting PCSK9","author":"Wu","year":"2018"},{"key":"2026103005080185500_cit3a","doi-asserted-by":"publisher","first-page":"381","DOI":"10.1093\/nsr\/nwx028","article-title":"Recent Progress in Organocatalytic Asymmetric Total Syntheses of Complex Indole Alkaloids","volume":"4","author":"Song","year":"2017","journal-title":"Natl. Sci. Rev."},{"key":"2026103005080185500_cit3b","doi-asserted-by":"publisher","first-page":"1388","DOI":"10.1002\/chem.201001451","article-title":"Structure, Bioactivity and Synthesis of Natural Products with Hexahydropyrrolo[2,3-b]indole","volume":"17","author":"Ruiz-Sanchis","year":"2011","journal-title":"Chem. Eur. J."},{"key":"2026103005080185500_cit3c","doi-asserted-by":"publisher","first-page":"5488","DOI":"10.1002\/anie.200700612","article-title":"Total Synthesis of Complex Cyclotryptamine Alkaloids: Stereocontrolled Construction of Quaternary Carbon Stereocenters","volume":"46","author":"Steven","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026103005080185500_cit3d","doi-asserted-by":"publisher","first-page":"151","DOI":"10.1021\/ar050175j","article-title":"Chemistry of the Hexahydropyrrolo[2,3-b]indoles: Configuration, Conformation, Reactivity, and Applications in Synthesis","volume":"40","author":"Crich","year":"2007","journal-title":"Acc. Chem. Res."},{"key":"2026103005080185500_cit4a","doi-asserted-by":"publisher","first-page":"2063","DOI":"10.1016\/j.tet.2019.02.006","article-title":"Recent Advances in Indoline Synthesis","volume":"75","author":"Silva","year":"2019","journal-title":"Tetrahedron"},{"key":"2026103005080185500_cit4b","doi-asserted-by":"publisher","first-page":"3975","DOI":"10.1002\/ejoc.201000323","article-title":"Diverse Strategies for the Synthesis of the Indoline Scaffold","volume":"2010","author":"Liu","year":"2010","journal-title":"Eur. J. Org. Chem."},{"key":"2026103005080185500_cit4c","doi-asserted-by":"publisher","first-page":"4275","DOI":"10.1021\/acs.orglett.7b01940","article-title":"2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of Indoles","volume":"19","author":"Abe","year":"2017","journal-title":"Org. Lett."},{"key":"2026103005080185500_cit4d","doi-asserted-by":"publisher","first-page":"16756","DOI":"10.1021\/ja509893s","article-title":"Ir-Catalyzed Reverse Prenylation of 3-Substituted Indoles: Total Synthesis of (+)-Aszonalenin and (\u2013)-Brevicompanine B","volume":"136","author":"Ruchti","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"2026103005080185500_cit4e","doi-asserted-by":"publisher","first-page":"4117","DOI":"10.1021\/ja400315y","article-title":"General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors: Enantioselective Total Syntheses of (+)- and (\u2013)-Gliocladine C, (+)-Leptosin D, (+)-T988C, (+)-Bionectin A, and (+)-Gliocladin A","volume":"135","author":"DeLorbe","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"2026103005080185500_cit4f","doi-asserted-by":"publisher","first-page":"1424","DOI":"10.1021\/ol300166q","article-title":"Intramolecular Oxidative Diamination and Aminohydroxylation of Olefins under Metal-Free Conditions","volume":"14","author":"Kim","year":"2012","journal-title":"Org. Lett."},{"key":"2026103005080185500_cit4g","doi-asserted-by":"publisher","first-page":"238","DOI":"10.1126\/science.1170777","article-title":"Total Synthesis of (+)-11,11\u2032-Dideoxyverticillin A","volume":"324","author":"Kim","year":"2009","journal-title":"Science"},{"key":"2026103005080185500_cit5","doi-asserted-by":"publisher","first-page":"4998","DOI":"10.1021\/acs.orglett.6c01163","article-title":"Modular Defluorinative Annulation Enabled by a Dearomative Rearrangement: Diversified Synthesis of Azaheterocycles","volume":"28","author":"Yang","year":"2026","journal-title":"Org. Lett."},{"key":"2026103005080185500_cit6a","doi-asserted-by":"publisher","first-page":"692","DOI":"10.1039\/p19780000692","article-title":"Reactions of Nitroarenes with Grignard Reagents General Method of Synthesis of Alkyl-Nitroso-Substituted Bicyclic Aromatic Systems","author":"Bartoli","year":"1978","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"2026103005080185500_cit6b","doi-asserted-by":"publisher","first-page":"4728","DOI":"10.1039\/c4cs00045e","article-title":"Applications of Bartoli Indole Synthesis","volume":"43","author":"Bartoli","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"2026103005080185500_cit6c","doi-asserted-by":"publisher","first-page":"197","DOI":"10.1055\/s-0040-1707250","article-title":"Concise Synthesis of Furo[2,3-b]indolines via [3,3]-Sigmatropic Rearrangement of N-Alkenyloxyindoles","volume":"32","author":"Shevlin","year":"2021","journal-title":"Synlett"},{"key":"2026103005080185500_cit6d","doi-asserted-by":"publisher","first-page":"3906","DOI":"10.1021\/acscatal.9b00470","article-title":"Copper-Catalyzed Tandem O-Vinylation of Arylhydroxylamines\/[3,3]-Rearrangement\/Cyclization: Synthesis of Highly Substituted Indoles and Benzoindoles","volume":"9","author":"Yuan","year":"2019","journal-title":"ACS Catal."},{"key":"2026103005080185500_cit7","volume":"28","author":"Liao","year":"2022","journal-title":"Chem.-Eur. J."},{"key":"2026103005080185500_cit8a","doi-asserted-by":"crossref","DOI":"10.1002\/9781118939901","volume-title":"Molecular Rearrangements in Organic Synthesis","author":"Rojas","year":"2015"},{"key":"2026103005080185500_cit8b","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1070\/RCR5039","article-title":"[3,3]\u2013Sigmatropic Rearrangements: a Variety of Methods and Recent Advances","volume":"91","author":"Dyachenko","year":"2022","journal-title":"Russ. Chem. Rev."},{"key":"2026103005080185500_cit9","article-title":"Gaussian, Inc","author":"Frisch","year":"2019"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c01446","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/doi\/10.1021\/acs.joc.6c01446\/68872284\/jo-2026-01446w.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/doi\/10.1021\/acs.joc.6c01446\/68872284\/jo-2026-01446w.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,30]],"date-time":"2026-10-30T09:21:39Z","timestamp":1793352099000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/43\/14097\/5451887\/Defluorinative-Annulation-Triggered-by-Lewis-Base"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,15]]},"references-count":29,"journal-issue":{"issue":"43","published-online":{"date-parts":[[2026,10,15]]},"published-print":{"date-parts":[[2026,10,30]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c01446","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,15]]}}}