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However, achieving its direct and chemoselective construction via O-arylation of amino alcohols remains a significant challenge in synthetic chemistry. Herein, we report a mild and efficient nickel-catalyzed C\u2013O cross-coupling of N-Boc-protected amino alcohols with (hetero)aryl halides. This method employs bipyridine as the ligand and an organic amine as the base, circumventing the need for specific ligand systems and strong inorganic bases typically required in other protocols. The system exhibits excellent functional group tolerance and broad compatibility, particularly with regard to heteroaryl halides and amino alcohols derived from natural amino acids. Furthermore, the scalability of the reaction is demonstrated through gram-scale synthesis, highlighting its potential for practical applications.<\/jats:p>","DOI":"10.1021\/acs.joc.6c00945","type":"journal-article","created":{"date-parts":[[2026,10,21]],"date-time":"2026-10-21T01:01:24Z","timestamp":1792544484000},"page":"13966-13971","source":"Crossref","is-referenced-by-count":0,"title":["Nickel-Catalyzed C\u2013O Cross-coupling of\n                    <i>N<\/i>\n                    -Boc-Protected Amino Alcohols with (Hetero)aryl Halides"],"prefix":"10.1021","volume":"91","author":[{"given":"Zi-Han","family":"Zhao","sequence":"first","affiliation":[{"name":"The Fourth Military Medical University , , , ,","place":["Xi\u2019an, Shaanxi, People\u2019s Republic of China, 710032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jia-Xin","family":"Feng","sequence":"additional","affiliation":[{"name":"The Fourth Military Medical University , , ,","place":["Xi\u2019an, People\u2019s Republic of China, 710032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gao-Dong","family":"Xu","sequence":"additional","affiliation":[{"name":"The Fourth Military Medical University , , ,","place":["Xi\u2019an, People\u2019s Republic of China, 710032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nan","family":"Ji","sequence":"additional","affiliation":[{"name":"The Fourth Military Medical University , , ,","place":["Xi\u2019an, People\u2019s Republic of China, 710032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-3279-8161","authenticated-orcid":true,"given":"Liu","family":"Yang","sequence":"additional","affiliation":[{"name":"School of Military Preventive Medicine, The Fourth Military Medical University , , , ,","place":["Xi\u2019an, Shaanxi, People\u2019s Republic of China, 710032"]},{"name":"The Fourth Military Medical University , , ,","place":["Xi\u2019an, People\u2019s Republic of China, 710032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7269-6356","authenticated-orcid":true,"given":"Dong","family":"Xue","sequence":"additional","affiliation":[{"name":"Shaanxi Normal University , , , ,","place":["Xi\u2019an, Shaanxi, People\u2019s Republic of China, 710119"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6703-6855","authenticated-orcid":true,"given":"Wei","family":"He","sequence":"additional","affiliation":[{"name":"The Fourth Military Medical University , , ,","place":["Xi\u2019an, People\u2019s Republic of China, 710032"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,20]]},"reference":[{"key":"2026103005075354500_cit1a","doi-asserted-by":"publisher","first-page":"703","DOI":"10.1007\/s00044-024-03215-1","article-title":"Phenoxyalkyl cyclic and acyclic amine derivatives: what do they teach us about scaffold-based drug design?","volume":"33","author":"Rezaeifar","year":"2024","journal-title":"Med. 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