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Here, we report that bidentate boronate coordination effectively suppresses this process, locking \u03b2-N-heterocycle enols into a rigid configuration to enable an efficient photochemical synthesis of \u03b2-N-heterocycle alcohols via a 1,5-boronate sigmatropic rearrangement. This strategy circumvents the inherent challenges of hydroxyl acidity and low \u03c0-electrophilicity characteristic of the ground-state enol manifold. Operating under mild, metal- and base-free conditions, this protocol facilitates the assembly of 61 diverse aromatic and nonaromatic \u03b2-N-heterocycle alcohols (up to 81% yield) using sp3-, sp2-, and sp-hybridized organoboronic acids. The methodology exhibits high chemo- and regioselectivity\u2500uniquely favoring 1,5-migration to the enol \u03b1-carbon over 1,3-addition to the imine\u2500and is well-suited for the late-stage functionalization of complex pharmaceuticals. Comprehensive mechanistic studies, integrating picosecond transient absorption (TA) spectroscopy with DFT modeling, identify a discrete excited-state triplet enol as the pivotal intermediate. Crucially, our findings demonstrate that these boronate\u2013enol photochemical transformations proceed via concerted sigmatropic pathways rather than previously assumed photoactivated nucleophilic additions. This work establishes a robust platform for exploiting coordination-induced kinetic control to modulate photochemical outcomes in enol-based substrates.<\/jats:p>","DOI":"10.1021\/jacsau.6c00455","type":"journal-article","created":{"date-parts":[[2026,6,12]],"date-time":"2026-06-12T02:11:22Z","timestamp":1781230282000},"page":"4458-4468","source":"Crossref","is-referenced-by-count":1,"title":["Photochemical Synthesis\nof \u03b2-N-Heterocycle\nAlcohols via a Coordination-Induced 1,5-Boronate Sigmatropic Rearrangement"],"prefix":"10.1021","volume":"6","author":[{"given":"Peng","family":"Zou","sequence":"first","affiliation":[{"name":"Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences , , 345 Lingling Road , ,","place":["Shanghai, China, 200032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dongmin","family":"Fu","sequence":"additional","affiliation":[{"name":"Zhengzhou University , , , ,","place":["Zhengzhou, Henan, China, 450001"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-0921-972X","authenticated-orcid":true,"given":"Jihao","family":"Jin","sequence":"additional","affiliation":[{"name":"Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences , , ,","place":["Beijing, China, 100190"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chenyang","family":"Xu","sequence":"additional","affiliation":[{"name":"Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences , , 345 Lingling Road , ,","place":["Shanghai, China, 200032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ruijing","family":"Cai","sequence":"additional","affiliation":[{"name":"Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences , , 345 Lingling Road , ,","place":["Shanghai, China, 200032"]},{"name":"ShanghaiTech University , , 100 Haike Road , ,","place":["Shanghai, China, 201210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9872-6245","authenticated-orcid":true,"given":"Shi-Jun","family":"Li","sequence":"additional","affiliation":[{"name":"Zhengzhou University , , , ,","place":["Zhengzhou, Henan, China, 450001"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0694-1795","authenticated-orcid":true,"given":"Yi","family":"Zeng","sequence":"additional","affiliation":[{"name":"Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences , , ,","place":["Beijing, China, 100190"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu","family":"Lan","sequence":"additional","affiliation":[{"name":"Zhengzhou University , , , ,","place":["Zhengzhou, Henan, China, 450001"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0916-0994","authenticated-orcid":true,"given":"Yiyun","family":"Chen","sequence":"additional","affiliation":[{"name":"Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences , , 345 Lingling Road , ,","place":["Shanghai, China, 200032"]},{"name":"ShanghaiTech University , , 100 Haike Road , ,","place":["Shanghai, China, 201210"]},{"name":"Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences , , 1 Sub-lane Xiangshan , ,","place":["Hangzhou, China, 310024"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,6,11]]},"reference":[{"key":"2026083023164835800_cit1a","doi-asserted-by":"publisher","first-page":"3841","DOI":"10.1021\/jm800009r","article-title":"1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles,\nNew Imidazoles with Potent Activity against Candida albicans and Dermatophytes.\nSynthesis, Structure\u2013Activity Relationship, and Molecular Modeling\nStudies","volume":"51","author":"La Regina","year":"2008","journal-title":"J. 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