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In contrast, exogenous binding\u2010where a guest selectively associates with the exterior surface, rather than the cavity, of its host owing to their size mismatch\u2010remains a largely unexplored paradigm for controlling the selectivity of chemical reactions. Here, we report that the exogenous binding between natural cyclodextrins (CDs) and a polyoxometalate catalyst leads to high site\u2010selectivity in hydrogen atom transfer between them. The decatungstate anion (W\n                    <jats:sub>10<\/jats:sub>\n                    O\n                    <jats:sub>32<\/jats:sub>\n                    <jats:sup>4\u2013<\/jats:sup>\n                    ), a photoactive polyoxometalate capable of abstracting hydrogen atoms from C\u2013H bonds on organic molecules, was found to associate noncovalently with CDs in aqueous solution. The large size of W\n                    <jats:sub>10<\/jats:sub>\n                    O\n                    <jats:sub>32<\/jats:sub>\n                    <jats:sup>4\u2013<\/jats:sup>\n                    , however, precludes the formation of deep inclusion complexes and confines its interactions with the narrow rim of CDs, as evidenced by\n                    <jats:sup>1<\/jats:sup>\n                    H NMR titration and x\u2010ray crystallography. This exogenous association increases the effective local concentration of W\n                    <jats:sub>10<\/jats:sub>\n                    O\n                    <jats:sub>32<\/jats:sub>\n                    <jats:sup>4\u2013<\/jats:sup>\n                    near the C6\u2013H bonds, accelerating HAT at these positions upon photoexcitation and rendering C6 functionalization kinetically dominant over slower, less selective background pathways. The host\u2010guest mismatch approach offers a general platform for the selective, one\u2010step ligations of CDs onto natural products, drugs, fluorescent probes as well as \u201cclick\u201d compatible molecular scaffolds.\n                  <\/jats:p>","DOI":"10.1002\/anie.4608575","type":"journal-article","created":{"date-parts":[[2026,7,21]],"date-time":"2026-07-21T19:13:01Z","timestamp":1784661181000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Host\u2013Guest Mismatch Enables Selective Hydrogen Atom Transfer"],"prefix":"10.1002","volume":"65","author":[{"given":"Yue","family":"Zhao","sequence":"first","affiliation":[{"name":"Department of Chemistry The University of Hong Kong  Hong Kong SAR China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yinian","family":"Tang","sequence":"additional","affiliation":[{"name":"Department of Chemistry The University of Hong Kong  Hong Kong SAR China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7332-5656","authenticated-orcid":false,"given":"Ching Ching","family":"Lam","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of California  Los Angeles California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ye","family":"Tao","sequence":"additional","affiliation":[{"name":"College of Chemistry and Environmental Engineering Shenzhen University  Shenzhen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhi","family":"Chen","sequence":"additional","affiliation":[{"name":"College of Chemistry and Environmental Engineering Shenzhen University  Shenzhen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Charlotte L.","family":"Stern","sequence":"additional","affiliation":[{"name":"Department of Chemistry Northwestern University  Evanston Illinois USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dengke","family":"Shen","sequence":"additional","affiliation":[{"name":"Institutes of Physical Science and Information Technology Anhui University  Hefei China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8883-0142","authenticated-orcid":false,"given":"Kang","family":"Cai","sequence":"additional","affiliation":[{"name":"College of Chemistry Nankai University  Tianjin China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4220-0919","authenticated-orcid":false,"given":"Zhou","family":"Ye","sequence":"additional","affiliation":[{"name":"Applied Oral Sciences and Community Dental Care, Faculty of Dentistry The University of Hong Kong  Hong Kong SAR China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaopeng","family":"Li","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences Chinese Academy of Sciences  Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8387-5261","authenticated-orcid":false,"given":"K. 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