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Transition-Metal-Free Oxidative Decarboxylative Cross Coupling of α,β-Unsaturated Carboxylic Acids with Cyclic Ethers under Air Conditions: Mild Synthesis of α‑Oxyalkyl Ketones
journal contribution
posted on 2017-02-22, 00:00 authored by Peng-Yi Ji, Yu-Feng Liu, Jing-Wen Xu, Wei-Ping Luo, Qiang Liu, Can-Cheng GuoA novel K2S2O8-promoted decarboxylative
cross coupling of α,β-unsaturated carboxylic acids with
cyclic ethers was developed under aerobic conditions. The present
protocol, which includes C–C and CO bond formation
in one step through addition, oxidation, and decarboxylation processes,
leads to the desired ketone products in moderate to excellent yields.
In addition, mechanism studies showed that the transformation process
undergoes a radical pathway via a direct activation of the α-sp3 C–H bond of oxygen of the cyclic ether.
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Transition-Metal-Free Oxidative Decarboxylative CrossCyclic Etherscyclic ethersOxyalkylcarboxylic acidsnovel K 2 S 2 O 8Mild Synthesisactivationketone productsoxidationKetonetransformation processdecarboxylativedecarboxylation processesα-spCarboxylicyieldUnsaturatedcyclic etherAir Conditionsmechanism studiespathwayAcidbond
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