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Here, a copper(I)\u2010catalyzed reaction of 2,6\u2010dibromo\u2010 and 2,6\u2010diiodophenols with diorganodiselenides has been studied for the introduction of two organoselenium substituents at both <jats:italic>ortho<\/jats:italic>\u2010positions of the phenolic radical chain\u2010breaking antioxidants, which afforded 2,6\u2010diorganoseleno\u2010substituted phenols in 80\u201392% yields having electron\u2010donating CH<jats:sub>3<\/jats:sub>, and electron\u2010withdrawing CN and CHO functionalities. Additionally, 2,6\u2010diiodophenols with electron\u2010withdrawing CHO and CN groups also afforded novel 5,5\u2032\u2010selenobis(4\u2010hydroxy\u20103\u2010(phenylselanyl)benzaldehyde) and 5,5\u2032\u2010selenobis(4\u2010hydroxy\u20103\u2010(phenylselanyl)benzonitrile) consisting of three selenium and two phenolic moieties along with 2,6\u2010diorganoseleno\u2010substituted phenols has been synthesized. The electron\u2010withdrawing CHO group has been reduced by sodium borohydride to the electron\u2010donating alcohol CH<jats:sub>2<\/jats:sub>OH group, which is desirable for efficient radical quenching activity of phenols. The developed copper\u2010catalyzed reaction conditions enable the installation of two\u2010arylselenium group <jats:italic>ortho<\/jats:italic> to phenolic radical chain\u2010breaking antioxidants, which may not be possible by conventional organolithium\u2010bromine exchange methods due to the sluggish reactivity of trianions (dicarba and phenoxide anion), which are generated by the reaction of organolithium with 2,6\u2010dibromophenols, with diorganodiselenides. The antioxidant activities of the synthesized bis and tris selenophenols have been accessed by DPPH, thiol peroxides, and singlet oxygen quenching assay. The radical quenching antioxidant activity has been studied for the synthesized compounds by 2,2\u2010diphenyl\u20101\u2010picrylhydrazyl (DPPH) assay. The bis\u2010selenophenols show comparable radical deactivating activity, while tris seleno\u2010bisphenols show higher radical deactivating activity than \u03b1\u2010tocopherol. Furthermore, the tris seleno\u2010bisphenol shows comparable peroxide decomposing activity with ebselen molecules.<\/jats:p>","DOI":"10.1002\/asia.202100139","type":"journal-article","created":{"date-parts":[[2021,3,4]],"date-time":"2021-03-04T00:30:23Z","timestamp":1614817823000},"page":"966-973","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["Radical Chain Breaking Bis(<i>ortho<\/i>\u2010organoselenium) Substituted Phenolic Antioxidants"],"prefix":"10.1002","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4072-062X","authenticated-orcid":false,"given":"Aditya","family":"Upadhyay","sequence":"first","affiliation":[{"name":"Department of Chemistry Indian Institute of Science Education and Research  Bhopal By-Pass Road Bhauri, Bhopal 462 066 Madhya Pradesh 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