2026-10-12T10:32:35Z https://api.figshare.com/v2/oai

oai:figshare.com:article/33963939 2026-09-22T10:11:15Z category_4 category_14 category_24 category_873 category_45 category_134 category_135 portal_63 item_type_3 month_year_09_2026

Synthesis of α‑Halophosphonates via Copper-Catalyzed Atom Transfer Radical Addition Jacob A. Utley (25089225) Tam D. Ho (13133526) Byung Joo Lee (2024926) Jake R. Elliott (25089228) Saurabh S. Satpute (25089231) Kami L. Hull (1493695) Biochemistry Molecular Biology Evolutionary Biology Chemical Sciences not elsewhere classified Sociology Virology Computational Biology tertiary haloalkanes add reducing agent regenerating product derivatization demonstrates mechanistic investigations support diazo compound serves commodity chemical industries 1 ′- azobis synthetic utility substituted vinylphosphonates substituted alkylphosphonates situ </ radical precursors optimized conditions including primary halophosphonates enabled excellent yields broad utility broad scope alkyl halides achn ). )] throughout α-Substituted alkylphosphonates and phosphates have broad utility in the pharmaceutical, agrochemical, and commodity chemical industries. Herein, we present the copper-catalyzed atom transfer radical addition (ATRA) of alkyl halides to alkenylphosphonates for the synthesis of α-halophosphonates enabled by 1,1′-azobis(cyclohexanecarbonitrile) (ACHN). Mechanistic investigations support that the diazo compound serves as an <i>in situ</i> reducing agent regenerating [Cu(I)] throughout the reaction and enabling high turnover numbers. Under the optimized conditions, a broad scope of radical precursors, including primary, secondary, and tertiary haloalkanes add to substituted vinylphosphonates in good to excellent yields. Product derivatization demonstrates the synthetic utility of the reaction. 2026-09-22T00:00:00Z Dataset Dataset 10.1021/acs.orglett.6c03586.s001 https://figshare.com/articles/dataset/Synthesis_of_Halophosphonates_via_Copper-Catalyzed_Atom_Transfer_Radical_Addition/33963939 CC BY-NC 4.0