Journal
ORGANIC LETTERS
Volume 20, Issue 10, Pages 3061-3064Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01058
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Funding
- National Basic Research Program of China [2015CB931903]
- National Natural Science Foundation [21421002, 21472222, 21502214, 21672242]
- Chinese Academy of Sciences [XDA02020105, XDA02020106]
- Key Research Program of Frontier Sciences (CAS) [QYZDJ-SSW-SLH049]
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An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. The use of (EtO)(3)P instead of Ph3P could also realize deoxy-halogenation, allowing for a convenient purification process, as the byproduct (EtO)(3)P=O could be removed by aqueous washing. The mild reaction conditions, wide substrate scope, and wide availability of 1,2-dihaloethanes make this protocol attractive for the synthesis of halogenated compounds.
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