Journal
ORGANIC LETTERS
Volume 20, Issue 22, Pages 7345-7350Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03345
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Funding
- NIH [S10 OD020022, S10 OD012245, GM098886]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM095666] Funding Source: NIH RePORTER
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A photocatalytic method for the oxyamination of alkenes using simple nucleophilic nitrogen atom sources in place of prefunctionalized electrophilic nitrogen atom donors is reported. Copper(II) is an inexpensive, practical, and uniquely effective terminal oxidant for this process. In contrast to oxygen, peroxides, and similar oxidants commonly utilized in non-photochemical oxidative methods, the use of copper(II) as a terminal oxidant in photoredox reactions avoids the formation of reactive heteroatom-centered radical intermediates that can be incompatible with electron-rich functional groups. As a demonstration of the generality of this concept, it has been shown that diamination and deoxygenation reactions can also be accomplished using similar photooxidative conditions.
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