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The water-soluble deep cavitand CV-1 serves as a multifunctional platform that synergistically addresses challenges of aqueous-phase macrocyclization, including poor substrate solubility, low cyclization selectivity, and unproductive side reactions of reactive intermediates. Specifically, CV-1 enables solubilization of hydrophobic linear \u03b1,\u03c9-dithiols in water, preorganizes them into folded J-shaped conformations favorable for intramolecular coupling, and sequesters reactive thiyl radical (RS\u00b7) intermediates within its confined cavity to suppress oligomerization. This interplay allows efficient aerobic oxidative cyclization under mild, metal-free conditions with ambient air as the sole oxidant, affording 8- to 14-membered cyclic disulfides in 61\u201389% yields. The cavitand cavity provides enduring stabilization of the encapsulated disulfide bonds, rendering them inert toward strong external reductants such as dithiothreitol (DTT). This work provides a preliminary demonstration of supramolecularly controlled macrocyclization in water, offering insights for future applications in biochemistry, pharmaceuticals, and materials science.<\/jats:p>","DOI":"10.1021\/jacs.6c15679","type":"journal-article","created":{"date-parts":[[2026,8,19]],"date-time":"2026-08-19T03:02:17Z","timestamp":1787108537000},"page":"36352-36358","source":"Crossref","is-referenced-by-count":0,"title":["Deep Cavitand Mediated\nSelective Aerobic Oxidative\nCyclization of Thiols to Cyclic Disulfides"],"prefix":"10.1021","volume":"148","author":[{"given":"Guangyu","family":"An","sequence":"first","affiliation":[{"name":"Shanghai University , , ,","place":["Shanghai, China, 200444"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haina","family":"Feng","sequence":"additional","affiliation":[{"name":"Shanghai University , , ,","place":["Shanghai, China, 200444"]},{"name":"Fudan University , , ,","place":["Shanghai, China, 200433"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zidi","family":"Wang","sequence":"additional","affiliation":[{"name":"ShanghaiTech University , , ,","place":["Shanghai, China, 201210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yujie","family":"Zhu","sequence":"additional","affiliation":[{"name":"Shanghai University , , ,","place":["Shanghai, China, 200444"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3990-8687","authenticated-orcid":true,"given":"Shan","family":"Jiang","sequence":"additional","affiliation":[{"name":"ShanghaiTech University , , ,","place":["Shanghai, China, 201210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2768-0945","authenticated-orcid":true,"suffix":"Jr.","given":"Julius","family":"Rebek","sequence":"additional","affiliation":[{"name":"Shanghai University , , ,","place":["Shanghai, China, 200444"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5698-3534","authenticated-orcid":true,"given":"Yang","family":"Yu","sequence":"additional","affiliation":[{"name":"Shanghai University , , ,","place":["Shanghai, China, 200444"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,18]]},"reference":[{"key":"2026090312083061100_cit1","doi-asserted-by":"publisher","first-page":"5768","DOI":"10.1021\/cr100006x","article-title":"Reactivity\nof Thioredoxin as a Protein Thiol-Disulfide Oxidoreductase","volume":"111","author":"Cheng","year":"2011","journal-title":"Chem. 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