Ag_(2)CO_(3)-promoted dehydroxymethylative fluorination of aliphatic alcohols has been achieved with Selectfluor as both oxidant and fluorine source.The reaction involvesβ-fragmentation of primary alkoxy radicals,fol...Ag_(2)CO_(3)-promoted dehydroxymethylative fluorination of aliphatic alcohols has been achieved with Selectfluor as both oxidant and fluorine source.The reaction involvesβ-fragmentation of primary alkoxy radicals,followed by the fluorination of the resulting C-centered radical intermediates.The transformation proceeds under mild reaction conditions and exhibits a broad substrate scope,thus opening up a new entrance to the synthesis of fluorinated constructs includingα-fluoroimides and 1-fluoroalkyl benzoates as well as secondary and tertiary alkyl fluorides like versatile 2-fluoro-2-alkyl 1,3-propandiol derivatives.The divergent functionalization of the obtainedα-fluoroimides enables an efficient access to amine derivatives through C-F bond activation under the action of BF_(3)·OEt_(2).展开更多
基金financial support from the Marine S&T Fund of Shandong Province for Pilot National Laboratory for Marine Science and Technology(Qingdao)(No.2022QNLM030003-2)the National Natural Science Foundation of China(No.21977088)the National Natural Science Foundation of China-Shandong Joint Fund(No.U1906213)。
文摘Ag_(2)CO_(3)-promoted dehydroxymethylative fluorination of aliphatic alcohols has been achieved with Selectfluor as both oxidant and fluorine source.The reaction involvesβ-fragmentation of primary alkoxy radicals,followed by the fluorination of the resulting C-centered radical intermediates.The transformation proceeds under mild reaction conditions and exhibits a broad substrate scope,thus opening up a new entrance to the synthesis of fluorinated constructs includingα-fluoroimides and 1-fluoroalkyl benzoates as well as secondary and tertiary alkyl fluorides like versatile 2-fluoro-2-alkyl 1,3-propandiol derivatives.The divergent functionalization of the obtainedα-fluoroimides enables an efficient access to amine derivatives through C-F bond activation under the action of BF_(3)·OEt_(2).
