Visible Light-Mediated Atom Transfer Radical Addition via Oxidative and Reductive Quenching of Photocatalysts
Herein, the development of visible light-mediated atom transfer radical addition (ATRA) of haloalkanes onto alkenes and alkynes using the reductive and oxidative quenching of [Ir{dF(CF3)ppy}2(dtbbpy)]PF6 and [Ru(bpy)3]Cl2 is presented. Initial investigations indicated that the oxidative quenching of...
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| Veröffentlicht in: | Journal of the American Chemical Society 2012-05, Vol.134 (21), p.8875-8884 |
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| container_issue | 21 |
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| container_title | Journal of the American Chemical Society |
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| creator | Wallentin, Carl-Johan Nguyen, John D Finkbeiner, Peter Stephenson, Corey R. J |
| description | Herein, the development of visible light-mediated atom transfer radical addition (ATRA) of haloalkanes onto alkenes and alkynes using the reductive and oxidative quenching of [Ir{dF(CF3)ppy}2(dtbbpy)]PF6 and [Ru(bpy)3]Cl2 is presented. Initial investigations indicated that the oxidative quenching of photocatalysts could effectively be utilized for ATRA, and since that report, the protocol has been expanded by broadening the scope of the reaction in terms of the photocatalysts, substrates, and solvents. In addition, further modifications of the reaction conditions allowed for the efficient ATRA of perfluoroalkyl iodides onto alkenes and alkynes utilizing the reductive quenching cycle of [Ru(bpy)3]Cl2 with sodium ascorbate as the sacrificial electron donor. These results signify the complementary nature of the oxidative and reductive quenching pathways of photocatalysts and the ability to predictably direct reaction outcome through modification of the reaction conditions. |
| doi_str_mv | 10.1021/ja300798k |
| format | Article |
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In addition, further modifications of the reaction conditions allowed for the efficient ATRA of perfluoroalkyl iodides onto alkenes and alkynes utilizing the reductive quenching cycle of [Ru(bpy)3]Cl2 with sodium ascorbate as the sacrificial electron donor. These results signify the complementary nature of the oxidative and reductive quenching pathways of photocatalysts and the ability to predictably direct reaction outcome through modification of the reaction conditions.</description><subject>Alkenes - chemistry</subject><subject>Alkylation</subject><subject>Alkynes - chemistry</subject><subject>Catalysis</subject><subject>Free Radicals - chemistry</subject><subject>Halogenation</subject><subject>Light</subject><subject>Oxidation-Reduction</subject><subject>Photochemical Processes</subject><subject>Solvents - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtPwzAQhC0EoqVw4A8gX5DgEPAjz2NV8ZKKgKpwjRx707okcYmdiv57XFp64rQ7q0-jnUHonJIbShi9XQhOSJKlnweoTyNGgoiy-BD1CSEsSNKY99CJtQsvQ5bSY9RjLPRXyvuo_tBWFxXgsZ7NXfAMSgsHCg-dqfG0FY0tocUTobQUFR4qpZ02DV5pgV--tRJOrwCLRuEJqE7-qrcOGjnXzQybEr_OjTNSOFGtrbOn6KgUlYWz3Ryg9_u76egxGL88PI2G40DwlLqAhTRNMimpyrI0SoCHoAr_MKRcxYxEPFakEH6VYRayJAJZhokijJEYopJyPkBXW99la746sC6vtZVQVaIB09mcEppkSRpGG_R6i8rWWNtCmS9bXYt27aF8026-b9ezFzvbrqhB7cm_Oj1wuQWEtPnCdG3jU_5j9AMzhoCl</recordid><startdate>20120530</startdate><enddate>20120530</enddate><creator>Wallentin, Carl-Johan</creator><creator>Nguyen, John D</creator><creator>Finkbeiner, Peter</creator><creator>Stephenson, Corey R. 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| source | ACS Publications; MEDLINE |
| subjects | Alkenes - chemistry Alkylation Alkynes - chemistry Catalysis Free Radicals - chemistry Halogenation Light Oxidation-Reduction Photochemical Processes Solvents - chemistry |
| title | Visible Light-Mediated Atom Transfer Radical Addition via Oxidative and Reductive Quenching of Photocatalysts |
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