{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T15:03:49Z","timestamp":1786719829167,"version":"build-2736575974"},"reference-count":80,"publisher":"American Chemical Society (ACS)","issue":"32","license":[{"start":{"date-parts":[[2026,8,3]],"date-time":"2026-08-03T00:00:00Z","timestamp":1785715200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,8,3]],"date-time":"2026-08-03T00:00:00Z","timestamp":1785715200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,8,3]],"date-time":"2026-08-03T00:00:00Z","timestamp":1785715200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100021171","name":"Basic and Applied Basic Research Foundation of Guangdong Province","doi-asserted-by":"publisher","award":["2022A1515110835"],"award-info":[{"award-number":["2022A1515110835"]}],"id":[{"id":"10.13039\/501100021171","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100021171","name":"Basic and Applied Basic Research Foundation of Guangdong Province","doi-asserted-by":"publisher","award":["2025A1515010088"],"award-info":[{"award-number":["2025A1515010088"]}],"id":[{"id":"10.13039\/501100021171","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["12504333"],"award-info":[{"award-number":["12504333"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Guangdong Provincial Key Laboratory of Mathematical and Neural Dynamical Systems","award":["2024B1212010004"],"award-info":[{"award-number":["2024B1212010004"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,14]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Bridged bicyclic scaffolds, particularly azacycle-fused bicyclo[2.1.1]hexanes, are three-dimensional bioisosteres of benzene in medicinal chemistry. We reported a computational study of BF3-catalyzed [2\u03c0 + 2\u03c3] cycloaddition between dihydropyridines (DHPs) and bicyclo[1.1.0]butanes (BCBs). Experimentally, this reaction exclusively affords the azacycle-fused product P1 (bond formation adjacent to the DHP nitrogen). To understand this selectivity, we also examined the hypothetical regioisomeric pathway to P2 (bond formation at the remote double bond). Our DFT and DLPNO\u2013CCSD(T)\/CBS calculations reveal a concerted BCB ring-opening and nucleophilic attack, revising the initially proposed stepwise mechanism. BF3 plays two distinct roles: it lowers the overall barrier via enhanced orbital interactions and reduced Pauli repulsion, and it reverses the intrinsic selectivity. Under catalyst-free conditions, P2 is unexpectedly favored due to superior dispersion interactions. Upon BF3 coordination, this dispersion advantage is eliminated through conformational changes, and differential electrostatic effects favor P1 over P2. Bulky C3 substituents such as t-Bu restore P2 preference with a moderate barrier, outperforming electron-withdrawing groups. An applied electric field lowers barriers without altering selectivity, while low-polarity solvents narrow the P1\/P2 barrier gap. Synergistically combining these parameters enables P2 formation with improved kinetics. This work provides mechanistic novelty and a multifactor strategy for rational selectivity control in strained-ring annulations.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01180","type":"journal-article","created":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T14:34:48Z","timestamp":1785854088000},"page":"10981-10990","source":"Crossref","is-referenced-by-count":0,"title":["Computational Insights\ninto BF3-Catalyzed\n[2\u03c0 + 2\u03c3] Cycloadditions: Catalyst, Substrate, Solvent,\nand Electric Field Effects"],"prefix":"10.1021","volume":"91","author":[{"given":"Ning","family":"Wang","sequence":"first","affiliation":[{"name":"Great Bay University , , ,","place":["Dongguan, China, 523000"]},{"name":"Southern University of Science and Technology , , ,","place":["Shenzhen, China, 518055"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuhong","family":"Yang","sequence":"additional","affiliation":[{"name":"Great Bay University , , ,","place":["Dongguan, China, 523000"]},{"name":"Southern University of Science and Technology , , ,","place":["Shenzhen, China, 518055"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0002-8758-7950","authenticated-orcid":true,"given":"Longhe","family":"Hu","sequence":"additional","affiliation":[{"name":"Changchun Institute of Technology , , ,","place":["Changchun, China, 130012"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5888-7933","authenticated-orcid":true,"given":"Dan","family":"Liu","sequence":"additional","affiliation":[{"name":"Changchun Institute of Technology , , ,","place":["Changchun, China, 130012"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0966-4343","authenticated-orcid":true,"given":"Xiaoyong","family":"Zhang","sequence":"additional","affiliation":[{"name":"Great Bay University , , ,","place":["Dongguan, China, 523000"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,3]]},"reference":[{"key":"2026081410094909400_cit1","doi-asserted-by":"publisher","first-page":"2493","DOI":"10.1039\/D5QO01662B","article-title":"Polysubstituted Bicyclo-[2.1.1]-Hexanes as Benzene\nIsosteres for Medicinal Chemistry","volume":"13","author":"Roa\u0300","year":"2026","journal-title":"Org. Chem.\nFront."},{"key":"2026081410094909400_cit2","doi-asserted-by":"publisher","first-page":"3829","DOI":"10.1021\/acs.chemrev.5c00779","article-title":"Smallest\nBicycles in Medicinal Chemistry: Where Are\nWe Now?","volume":"126","author":"Kubyshkin","year":"2026","journal-title":"Chem. Rev."},{"key":"2026081410094909400_cit3","doi-asserted-by":"publisher","first-page":"21615","DOI":"10.1021\/acs.jmedchem.5c01879","article-title":"Beyond Bioisosteres:\nImpact of Replacing a Benzene Ring with sp3 -Rich Three-Dimensional\nSaturated Bridged Bicyclic Match Pairs on Biotransformation, Metabolic\nStability, and Other ADME Profiles","volume":"68","author":"Surendran","year":"2025","journal-title":"J. Med.\nChem."},{"key":"2026081410094909400_cit4","doi-asserted-by":"publisher","first-page":"6417","DOI":"10.1039\/D5CC00816F","article-title":"Recent advances\nin bridged structures as 3D bioisosteres of ortho-phenyl rings in\nmedicinal chemistry applications","volume":"61","author":"Xia","year":"2025","journal-title":"Chem. Commun."},{"key":"2026081410094909400_cit5","doi-asserted-by":"publisher","first-page":"605","DOI":"10.1038\/s41570-024-00623-0","article-title":"Three-dimensional saturated C(sp3)-rich bioisosteres for\nbenzene","volume":"8","author":"Tsien","year":"2024","journal-title":"Nat.\nRev. Chem."},{"key":"2026081410094909400_cit6","doi-asserted-by":"publisher","first-page":"2839","DOI":"10.1039\/C8OB02812E","article-title":"Saturated\nbioisosteres of benzene: where to go next?","volume":"17","author":"Mykhailiuk","year":"2019","journal-title":"Org. Biomol. Chem."},{"key":"2026081410094909400_cit7","doi-asserted-by":"publisher","first-page":"4634","DOI":"10.1021\/acscatal.5c00303","article-title":"Lewis Acid-Catalyzed\nAsymmetric [2\u03c3 + 2\u03c0] Cycloaddition Reactions of Bicyclo[1.1.0]butanes\nand Vinyl Azido\/Diazo Compounds","volume":"15","author":"Ren","year":"2025","journal-title":"ACS Catal."},{"key":"2026081410094909400_cit8","doi-asserted-by":"publisher","first-page":"6942","DOI":"10.1039\/D4QO01741B","article-title":"State-of-the-Art Strategies\nfor Lewis Acid-Catalyzed Strain-Release Cycloadditions of Bicyclo[1.1.0]Butanes\n(BCBs)","volume":"11","author":"Liu","year":"2024","journal-title":"Org. Chem. Front."},{"key":"2026081410094909400_cit9","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202304771","article-title":"Lewis Acid\nCatalyzed Formal (3 +\n2)-Cycloaddition of Bicyclo[1.1.0]Butanes with Ketenes","volume":"62","author":"Radhoff","year":"2023","journal-title":"Angew. Chem., Int. 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Ed."},{"key":"2026081410094909400_cit12","doi-asserted-by":"publisher","first-page":"9361","DOI":"10.1038\/s41467-025-64399-7","article-title":"Organocatalytic enantioselective\n[2\u03c0 + 2\u03c3] cycloaddition reactions of bicyclo[1.1.0]butanes\nwith \u03b1,\u03b2-unsaturated aldehydes","volume":"16","author":"Geng","year":"2025","journal-title":"Nat. Commun."},{"key":"2026081410094909400_cit13","doi-asserted-by":"publisher","first-page":"364","DOI":"10.1039\/D5QO01029B","article-title":"Enantioselective\npolar\n[2\u03c3 + 2\u03c0] cycloadditions of bicyclo[1.1.0]butanes and\northo-quinone methides enabled by chiral phosphoric acid catalysis","volume":"13","author":"Xu","year":"2026","journal-title":"Org. Chem. 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Soc."},{"key":"2026081410094909400_cit19","doi-asserted-by":"publisher","first-page":"35755","DOI":"10.1021\/jacs.5c12057","article-title":"Asymmetric Dearomative\n[2 + 2] Photocycloaddition of Quinoline and Indole Derivatives with\nBicyclo[1.1.0]Butanes","volume":"147","author":"Yang","year":"2025","journal-title":"J. Am. Chem. 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Synth."},{"key":"2026081410094909400_cit22","doi-asserted-by":"publisher","first-page":"229","DOI":"10.1021\/acs.orglett.4c04224","article-title":"Palladium-Catalyzed Strain-Enabled [2\u03c0+2\u03c3]\nCycloadditions of Vinyl Bicyclo[1.1.0]Butanes with Methyleneindolinones","volume":"27","author":"Zheng","year":"2025","journal-title":"Org. Lett."},{"key":"2026081410094909400_cit23","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202505060","article-title":"Direct Access to Functional 2-Azabicyclo[2.1.1]Hexanes\nvia Hydrodearomative\n[2\u03c0 + 2\u03c3] Cycloaddition of Aza-Arenes","volume":"64","author":"Yang","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081410094909400_cit24","doi-asserted-by":"publisher","first-page":"15698","DOI":"10.1021\/acscatal.5c03898","article-title":"Dual Au(I) Catalysis in Regioselective\nCycloaddition of Bicyclo[1.1.0]butanes with Allenes","volume":"15","author":"Giovanelli","year":"2025","journal-title":"ACS Catal."},{"key":"2026081410094909400_cit25","doi-asserted-by":"publisher","first-page":"535","DOI":"10.1038\/s41557-023-01135-y","article-title":"A Catalytic Alkene\nInsertion Approach\nto Bicyclo[2.1.1]Hexane Bioisosteres","volume":"15","author":"Agasti","year":"2023","journal-title":"Nat. Chem."},{"key":"2026081410094909400_cit26","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202420831","article-title":"Diverse Synthesis of\nArene-Fused [n.1.1]-Bridged Molecules\nvia Catalytic Cycloaddition and Rearrangement Reactions","volume":"64","author":"Yu","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081410094909400_cit27","doi-asserted-by":"publisher","first-page":"13755","DOI":"10.1021\/jacs.5c20918","article-title":"Enantioselective [2\u03c0+2\u03c3] Cycloaddition\nto Bicyclo[2.1.1]hexanes Enabled by an Artificial Photoenzyme","volume":"148","author":"Li","year":"2026","journal-title":"J. Am. Chem. Soc."},{"key":"2026081410094909400_cit28","doi-asserted-by":"publisher","first-page":"1120","DOI":"10.1007\/s11426-025-2941-2","article-title":"Controllable Divergent Transformations of Bicyclo[1.1.0]Butanes","volume":"69","author":"He","year":"2026","journal-title":"Sci. China: Chem."},{"key":"2026081410094909400_cit29","doi-asserted-by":"publisher","first-page":"2738","DOI":"10.1021\/jacsau.5c00341","article-title":"Catalyst-Controlled\nDivergent Synthesis of Bicyclo[2.1.1]Hexanes and Cyclobutenes: The\nUnique Effect of Au(I)","volume":"5","author":"Lu","year":"2025","journal-title":"JACS Au"},{"key":"2026081410094909400_cit30","doi-asserted-by":"publisher","first-page":"7633","DOI":"10.1021\/acs.orglett.5c02160","article-title":"Precise\nModulation of BCB Reactive Sites via Lewis\/Br\u00f8nsted Acid Switching\nfor the Synthesis of Spirocycles and Bridged Frameworks","volume":"27","author":"Li","year":"2025","journal-title":"Org. Lett."},{"key":"2026081410094909400_cit31","doi-asserted-by":"publisher","first-page":"27830","DOI":"10.1021\/jacs.4c10153","article-title":"Divergent Enantioselective\nAccess to Diverse Chiral\nCompounds from Bicyclo[1.1.0]Butanes and \u03b1,\u03b2-Unsaturated\nKetones under Catalyst Control","volume":"146","author":"Jeong","year":"2024","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026081410094909400_cit32","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202405222","article-title":"Switching between the [2\u03c0 + 2\u03c3] and Hetero-[4\u03c0+2\u03c3]\nCycloaddition Reactivity of Bicyclobutanes with Lewis Acid Catalysts\nEnables the Synthesis of Spirocycles and Bridged Heterocycles","volume":"63","author":"Wang","year":"2024","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081410094909400_cit33","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202408578","article-title":"Divergent Synthesis of Sulfur-Containing Bridged Cyclobutanes\nby Lewis Acid Catalyzed Formal Cycloadditions of Pyridinium 1,4-Zwitterionic\nThiolates and Bicyclobutanes","volume":"63","author":"Xiao","year":"2024","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026081410094909400_cit34","doi-asserted-by":"publisher","first-page":"1392","DOI":"10.1021\/acs.orglett.5c05244","article-title":"HFIP-Mediated (3\n+ 2) Annulation of Bicyclobutanes\nwith Indolyl Alcohols for Diastereoselective Access to Tetracyclic\nSpiroindolenines","volume":"28","author":"Deswal","year":"2026","journal-title":"Org. Lett."},{"key":"2026081410094909400_cit35","doi-asserted-by":"publisher","first-page":"18565","DOI":"10.1021\/jacs.4c04485","article-title":"Synthesis of Azabicyclo[3.1.1]Heptenes\nEnabled by Catalyst-Controlled Annulations of Bicyclo[1.1.0]Butanes\nwith Vinyl Azides","volume":"146","author":"Lin","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026081410094909400_cit36","doi-asserted-by":"publisher","first-page":"4925","DOI":"10.1021\/acscatal.5c08928","article-title":"Strain-Release-Driven\n[4+ 1] Annulation: Leveraging Bicyclo[1.1.0]Butanes as C1 Synthons\nvia Rh(III) Carbenoid","volume":"16","author":"Zhang","year":"2026","journal-title":"ACS Catal."},{"key":"2026081410094909400_cit37","doi-asserted-by":"publisher","first-page":"14936","DOI":"10.1021\/jacs.5c02425","article-title":"Catalyst-Controlled\nRegiodivergent Synthesis of Bicyclo[2.1.1]hexanes via Photochemical\nStrain-Release Cycloadditions","volume":"147","author":"Chang","year":"2025","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026081410094909400_cit38","doi-asserted-by":"publisher","first-page":"112369","DOI":"10.1016\/j.cclet.2026.112369","article-title":"Palladium-catalyzed\nand ligand-controlled regiodivergent intramolecular cyclization of\nketone-vinylbicyclo[1.1.0]butanes (Ketone-VC-BCBs)","volume":"20","author":"Yan","year":"2026","journal-title":"Chin. Chem. Lett."},{"key":"2026081410094909400_cit39","doi-asserted-by":"publisher","first-page":"6216","DOI":"10.1038\/s41467-025-61415-8","article-title":"Regiodivergent hydrophosphination\nof Bicyclo[1.1.0]-Butanes under catalyst control","volume":"16","author":"Huang","year":"2025","journal-title":"Nat. Commun."},{"key":"2026081410094909400_cit40","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202506228","article-title":"Lewis Acid\nCatalyzed Divergent Reaction of Bicyclo[1.1.0]Butanes With Quinones\nfor the Synthesis of Diverse Polycyclic Molecules","volume":"64","author":"Hu","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"issue":"146","key":"2026081410094909400_cit41","doi-asserted-by":"publisher","first-page":"19621","DOI":"10.1021\/jacs.4c01851","article-title":"Palladium-Catalyzed\nLigand-Controlled Switchable Hetero-(5 + 3)\/Enantioselective [2\u03c3+2\u03c3]\nCycloadditions of Bicyclobutanes with Vinyl Oxiranes","volume":"146","author":"Zhou","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026081410094909400_cit42","doi-asserted-by":"publisher","first-page":"6025","DOI":"10.1021\/acscatal.4c07205","article-title":"Conditions-Controlled Divergent Annulation\nof Bicyclo[1.1.0]Butanes and Dioxopyrrolidines through Lewis Acid\nCatalysis","volume":"15","author":"Li","year":"2025","journal-title":"ACS Catal."},{"key":"2026081410094909400_cit43","doi-asserted-by":"publisher","first-page":"5908","DOI":"10.1039\/D5QO00799B","article-title":"Lewis acid catalyzed\ndivergent annulation of bicyclo[1.1.0]butanes\nand quinones for the synthesis of various polycyclic molecules","volume":"12","author":"Meher","year":"2025","journal-title":"Org. Chem. Front."},{"key":"2026081410094909400_cit44","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202418239","article-title":"Solvent-Dependent Divergent Cyclization of Bicyclo[1.1.0]Butanes","volume":"64","author":"Zhang","year":"2025","journal-title":"Angew. Chem., Int. 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