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oai:figshare.com:article/34021124 2026-09-29T04:14:20Z category_4 category_21 category_24 category_873 category_45 category_61 category_133 portal_63 item_type_6 month_year_09_2026

Regio- and Stereoselective 1,4-(Hetero)arylalkylation of Isoprene by Photoredox Catalysis Xin Wang (91924) Yaning Han (841545) Renxu Cao (20459564) Xiaobo Ding (115597) Lei Shi (8144) Biochemistry Biotechnology Evolutionary Biology Chemical Sciences not elsewhere classified Sociology Developmental Biology Plant Biology synthetically useful yields sup >+</ sup stereocontrol (> 20 achieves exclusive regioselectivity 2 -, 3 affording functionalized isoprenes 4 -( hetero 4 -, 1 functionalized adducts 4 -, z </ visible light using mes standing challenge selective approach protocol offers primarily due organic photocatalyst free photoredox e </ bulk chemical annual production amino radicals Selective difunctionalization of isoprene, a bulk chemical with annual production, remains a long-standing challenge, primarily due to competing 1,2-, 3,4-, 1,4-, and 4,1-additions and <i>E</i>:<i>Z</i> isomerism. We report a metal-free photoredox-catalyzed 1,4-arylalkylation via arene C–H functionalization that achieves exclusive regioselectivity and outstanding <i>E</i>:<i>Z</i> stereocontrol (>20:1). Using Mes-Acr⁺BF₄^– as an organic photocatalyst under visible light, the reaction accommodates various arenes and imines, affording functionalized isoprenes in synthetically useful yields. Mechanistic studies indicate sequential radical addition and cross-coupling of allylic and α-amino radicals. This protocol offers a direct and selective approach to 1,4-functionalized adducts. 2026-09-29T00:00:00Z Text Journal contribution 10.1021/acs.orglett.6c03598.s001 https://figshare.com/articles/journal_contribution/Regio-_and_Stereoselective_1_4-_Hetero_arylalkylation_of_Isoprene_by_Photoredox_Catalysis/34021124 CC BY-NC 4.0