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The synergistic effects of Tl(OCOCF3)3 and a Pd\u2013thioether ligand catalytic system enabled electrophilic C\u2013H bond activation, followed by Heck-type alkenylation at the C8 position of the coumarin ring, affording a series of C8-alkenylated dimethoxycoumarin derivatives in yields of up to 90%. Notably, the bimetallic catalytic system promoted electrophilic C\u2013H activation of electron-rich coumarin scaffolds using only a catalytic amount of Tl(OCOCF3)3, enabling efficient C\u2013H functionalization of the benzene moiety with excellent regioselectivity. This method provides a versatile and step-economical approach to highly functionalized coumarins and serves as a complementary strategy for the late-stage functionalization of coumarin-based natural products and fluorescent compounds.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01609","type":"journal-article","created":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T19:01:28Z","timestamp":1791313288000},"page":"14227-14234","source":"Crossref","is-referenced-by-count":0,"title":["Pd\/Tl Bimetal-Catalyzed C8\u2013H Alkenylation of Dimethoxycoumarins"],"prefix":"10.1021","volume":"91","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1196-2737","authenticated-orcid":true,"given":"Takahiro","family":"Yamada","sequence":"first","affiliation":[{"name":"Kobe Pharmaceutical University , 4-19-1, Motoyamakita, Higashinada , ,","place":["Kobe, Japan, 658-8558"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rinka","family":"Fujita","sequence":"additional","affiliation":[{"name":"Kobe Pharmaceutical University , 4-19-1, Motoyamakita, Higashinada , ,","place":["Kobe, Japan, 658-8558"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ayaka","family":"Kishino","sequence":"additional","affiliation":[{"name":"Kobe Pharmaceutical University , 4-19-1, Motoyamakita, Higashinada , ,","place":["Kobe, Japan, 658-8558"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2330-0201","authenticated-orcid":true,"given":"Norihiko","family":"Takeda","sequence":"additional","affiliation":[{"name":"Kobe Pharmaceutical University , 4-19-1, Motoyamakita, Higashinada , ,","place":["Kobe, Japan, 658-8558"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8003-2971","authenticated-orcid":true,"given":"Masafumi","family":"Ueda","sequence":"additional","affiliation":[{"name":"Kobe Pharmaceutical University , 4-19-1, Motoyamakita, Higashinada , ,","place":["Kobe, Japan, 658-8558"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,6]]},"reference":[{"issue":"20","key":"2026103005070909000_cit1","doi-asserted-by":"publisher","first-page":"10476","DOI":"10.1021\/cr500075s","article-title":"Natural and synthetic chromenes, fused chromenes, and versatility of dihydrobenzo[h]chromenes in organic synthesis","volume":"114","author":"Pratap","year":"2014","journal-title":"Chem. 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