Journal
ORGANIC LETTERS
Volume 23, Issue 22, Pages 8968-8972Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03488
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Funding
- National Natural Science Foundation of China [21901197]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
- Xi'an Jiaotong University (XJTU)
- Natural Science Basic Research Plan in Shaanxi Province of China [2021JM004]
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The experiment presents a general photocatalytic method for the remote C(sp(3))-H bond amination of free aliphatic alcohols, utilizing electron transfer between FeCl3 catalyst and alkanols under blue LED irradiation. It enables alkoxy radical formation under mild redox-neutral conditions without the need for additional oxidants and prefunctionalization. The subsequent selective 1,5-hydrogen atom transfer (HAT) and amination offer a simple and efficient way to access molecular complexity from readily available and bulk alcohols.
We report a general photocatalytic protocol for the remote C(sp(3))-H bond amination of free aliphatic alcohols. The electron transfer between the abundant and inexpensive catalyst FeCl3 and simple alkanols under blue LED irradiation enables the alkoxy radical formation under mild redox-neutral conditions, with no need for additional oxidant and prefunctionalization. The subsequent selective 1,5-hydrogen atom transfer (HAT) and amination provide a simple and efficient way to access molecular complexity from readily available and bulk alcohols.
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