期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 21, 页码 8875-8884出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja300798k
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资金
- NSF [CHE-1056568]
- Alfred P. Sloan Foundation
- Amgen
- Boehringer Ingelheim
- Swedish Research Council
- Royal Physiographic Society in Lund
- AstraZeneca
- DAAD RISE
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1056568] Funding Source: National Science Foundation
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)]Cl-2 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)]Cl-2 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.
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