{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T01:43:05Z","timestamp":1791423785344,"version":"4.3.3"},"reference-count":44,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2025,1,22]],"date-time":"2025-01-22T00:00:00Z","timestamp":1737504000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000893","name":"Simons Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100000893","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000054","name":"National Cancer Institute","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100000054","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["advanced.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Adv Synth Catal"],"published-print":{"date-parts":[[2025,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Phosphorus Fluoride Exchange (PFEx) is a new click chemistry technology that hinges on the creation of innovative hubs to unlock its potential and broaden its applications. In this study, we outline some guiding principles for PFEx hub development and validate these principles by developing a new hub, 2\u2010substituted\u2010alkynyl\u20101\u2010cyclotriphosphazenes (SACPs). These SACPs serve as versatile PFEx hubs with stable functionality and orthogonal reactivity, exemplifying their utility within the Diversity Oriented Clicking (DOC) framework. We demonstrate that SACPs interact with various 1,3\u2010dipoles, enabling the synthesis of phosphorus\u2010rich compounds through sequential cycloaddition and PFEx reactions, thus pioneering new synthetic routes for wide application of click chemistry.<\/jats:p>","DOI":"10.1002\/adsc.202401573","type":"journal-article","created":{"date-parts":[[2025,1,7]],"date-time":"2025-01-07T22:41:23Z","timestamp":1736289683000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Phosphorus Fluoride Exchange (PFEx) Click Chemistry: 2\u2010Substituted\u2010Alkynyl\u20101\u2010Cyclotriphosphazene (SACP) Hubs for Diversity Oriented Clicking"],"prefix":"10.1002","volume":"367","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6835-695X","authenticated-orcid":false,"given":"Zifei","family":"Wang","sequence":"first","affiliation":[{"name":"Cancer Center Cold Spring Harbor Laboratory  1 Bungtown Road Cold Spring Harbor NY-11724 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3298-0600","authenticated-orcid":false,"given":"Dharmendra S.","family":"Vishwakarma","sequence":"additional","affiliation":[{"name":"Cancer Center Cold Spring Harbor Laboratory  1 Bungtown Road Cold Spring Harbor NY-11724 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7650-0437","authenticated-orcid":false,"given":"Shoujun","family":"Sun","sequence":"additional","affiliation":[{"name":"Cancer Center Cold Spring Harbor Laboratory  1 Bungtown Road Cold Spring Harbor NY-11724 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0002-7995-4781","authenticated-orcid":false,"given":"Qiyao","family":"Huang","sequence":"additional","affiliation":[{"name":"Cancer Center Cold Spring Harbor Laboratory  1 Bungtown Road Cold Spring Harbor NY-11724 USA"},{"name":"Department of Chemistry Stony Brook University  Nicolls Road Stony Brook NY-11794 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4552-6076","authenticated-orcid":false,"given":"Soumyaranjan","family":"Pati","sequence":"additional","affiliation":[{"name":"Cancer Center Cold Spring Harbor Laboratory  1 Bungtown Road Cold Spring Harbor NY-11724 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3023-8971","authenticated-orcid":false,"given":"Robert M.","family":"Johnson","sequence":"additional","affiliation":[{"name":"Cancer Center Cold Spring Harbor Laboratory  1 Bungtown Road Cold Spring Harbor NY-11724 USA"},{"name":"Department of Chemistry Stony Brook University  Nicolls Road Stony Brook NY-11794 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6128-2326","authenticated-orcid":false,"given":"Michael R.","family":"Rufrano","sequence":"additional","affiliation":[{"name":"Cancer Center Cold Spring Harbor Laboratory  1 Bungtown Road Cold Spring Harbor NY-11724 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3898-1612","authenticated-orcid":false,"given":"Milan","family":"Gembicky","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of California  San Diego La Jolla CA-92093 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7881-7761","authenticated-orcid":false,"given":"Joshua A.","family":"Homer","sequence":"additional","affiliation":[{"name":"Cancer Center Cold Spring Harbor Laboratory  1 Bungtown Road Cold Spring Harbor NY-11724 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2162-3234","authenticated-orcid":false,"given":"John E.","family":"Moses","sequence":"additional","affiliation":[{"name":"Cancer Center Cold Spring Harbor Laboratory  1 Bungtown Road Cold Spring Harbor NY-11724 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,1,22]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2023.05.013"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309399"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202003219"},{"key":"e_1_2_6_5_1","first-page":"435","volume-title":"Science of Synthesis: Click Chemistry","author":"Giel M.-C.","year":"2021"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2208540119"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CC04473K"},{"key":"e_1_2_6_8_1","author":"Kop J. W.","year":"2024","journal-title":"Org. Lett."},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC03400A"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01309"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC00986D"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201712145"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201902489"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-021-00726-x"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201915519"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202207456"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.xpro.2023.102824"},{"key":"e_1_2_6_18_1","volume-title":"Best Synthetic Methods: Organophosphorus (V) Chemistry","author":"Timperley C.","year":"2014"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196907811"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19731061016"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol3025154"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/p19850002621"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2007.11.124"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02794"},{"key":"e_1_2_6_25_1","unstructured":"Gaussian 16 Software Was Used to Conduct These Calculations. Gaussian 16 Revision C.02 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 D. Williams-Young 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 and D.\u2005J. Fox Gaussian Inc. Wallingford CT 2016."},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic951065j"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic0001863"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1080\/10426509508042512"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10973-015-4737-3"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1039\/dt9840002843"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1080\/00945718608071393"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1080\/10426507.2014.905864"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2013.05.020"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic100703h"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2023.03.017"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756360903524304"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.202100188"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2018.05.013"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6NJ03181A"},{"key":"e_1_2_6_41_1","unstructured":"The lower yield of isoxazole4\u2009g(25%) was attributed to limited stability on silica gel."},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c01046"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202400680"},{"key":"e_1_2_6_44_1","unstructured":"F. Hoffmann-Emery K. Puentener H. Ratni Process for the Preparation of Pyrollidine-3-Carboxylic Acids 2013 US8344161B2."},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.csite.2024.104383"}],"container-title":["Advanced Synthesis &amp; Catalysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/adsc.202401573","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,6]],"date-time":"2025-10-06T13:35:38Z","timestamp":1759757738000},"score":1,"resource":{"primary":{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/10.1002\/adsc.202401573"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,1,22]]},"references-count":44,"journal-issue":{"issue":"7","published-print":{"date-parts":[[2025,4]]}},"alternative-id":["10.1002\/adsc.202401573"],"URL":"https:\/\/doi.org\/10.1002\/adsc.202401573","archive":["Portico"],"relation":{},"ISSN":["1615-4150","1615-4169"],"issn-type":[{"value":"1615-4150","type":"print"},{"value":"1615-4169","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,1,22]]},"assertion":[{"value":"2024-12-19","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-01-22","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202401573"}}