期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 29, 页码 9799-9802出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b05082
关键词
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资金
- NSF [CHE-1565085]
- ACS-PRF [57164-ND1]
- National Natural Science Foundation of China [21572055, 21372073]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1565085] Funding Source: National Science Foundation
An unprecedented, chemo- and regioselective, organo-photoredox catalyzed hydroformylation reaction of aryl olefins with diethoxyacetic acid as the formylation reagent is described. In contrast to traditional transition metal promoted ionic hydroformylation reactions, the new process follows a unique photoredox promoted, free radical pathway. In this process, a formyl radical equivalent, produced from diethoxacetic acid through a dye (4CzIPN) photocatalyzed, sequential oxidation decarboxylation route, regio- and chemoseleclively adds to a styrene substrate. Importantly, under the optimized reaction conditions the benzylic radical formed in this manner is reduced by SET from the anion radical of 4CzIPN to generate a benzylic anion. Finally, protonation produces the hydroformylation product. By using the new protocol, aldehydes can be generated regioselectively in up to 90% yield. A broad array of functional groups is tolerated in the process, which takes place under mild, metal-free conditions.
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