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When using polar solvent 1,1,1,3,3,3-hexafluoro-2-propane (HFIP) with K2CO3, the C\u2013H annulation selectively delivered 5-arylnaphtho[1\u2032,2\u2032:4,5]imidazo[1,2-a]pyridine. In contrast, a system with nonpolar solvent p-xylene with NaOAc predominately afforded 3-substituted 2-arylimidazo[1,2-a]pyridines via C3\u2013H functionalization. The developed reaction methodology features a wide substrate scope and ideal functional group tolerance. It is also operationally simple and scalable. Furthermore, the photophysical properties of annulation products and further derivatizations of C3\u2013H functional products demonstrate that this method has potential applications in photoelectric materials and organic synthesis. Through a combined computational and experimental mechanistic study, we delineate the distinct roles of the solvent and base.<\/jats:p>","DOI":"10.1021\/acs.joc.6c00670","type":"journal-article","created":{"date-parts":[[2026,8,6]],"date-time":"2026-08-06T07:01:50Z","timestamp":1785999710000},"page":"10827-10835","source":"Crossref","is-referenced-by-count":0,"title":["Solvent\/Base-Cocontrolled\nRegiodivergent Synthesis\nof 5-Arylnaphtho[1\u2032,2\u2032:4,5]imidazo[1,2-\n                    <i>a<\/i>\n                    ]pyridines and 3-Substituted 2-Arylimidazo[1,2-\n                    <i>a<\/i>\n                    ]pyridines from 2-Arylimidazo[1,2-\n                    <i>a<\/i>\n                    ]pyridines and \u03b1-Cl Ketones via a Rh(III)-Catalyzed\nC\u2013H Activation Strategy"],"prefix":"10.1021","volume":"91","author":[{"given":"Tao","family":"Chen","sequence":"first","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhimeng","family":"Wang","sequence":"additional","affiliation":[{"name":"Shenyang Normal University , , , ,","place":["Shenyang, Liaoning, China, 110034"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ning","family":"Xu","sequence":"additional","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhishuang","family":"Du","sequence":"additional","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wangze","family":"Li","sequence":"additional","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Baoheng","family":"Wu","sequence":"additional","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tianyi","family":"Liu","sequence":"additional","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenrui","family":"Li","sequence":"additional","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ye","family":"Lu","sequence":"additional","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinxin","family":"Jin","sequence":"additional","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liang","family":"Xu","sequence":"additional","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinglin","family":"Liu","sequence":"additional","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0644-9971","authenticated-orcid":true,"given":"Fengyang","family":"Bai","sequence":"additional","affiliation":[{"name":"Shenyang Normal University , , , ,","place":["Shenyang, Liaoning, China, 110034"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weilei","family":"Zhou","sequence":"additional","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3588-0215","authenticated-orcid":true,"given":"He","family":"Li","sequence":"additional","affiliation":[{"name":"Inner Mongolia Minzu University , , ,","place":["Tongliao, China, 028000"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,6]]},"reference":[{"key":"2026081410095876200_cit1","doi-asserted-by":"publisher","first-page":"347","DOI":"10.1016\/S0960-894X(02)01020-X","article-title":"Imidazopyr-imidines,\nPotent Inhibitors of p38 MAP Kinase","volume":"13","author":"Rupert","year":"2003","journal-title":"Bioorg.\nMed. 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