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Regioselective Arene and Heteroarene Functionalization: N‑Alkenoxypyridinium Salts as Electrophilic Alkylating Agents for the Synthesis of α‑Aryl/α-Heteroaryl Ketones
journal contributionposted on 2018-07-18, 00:00 authored by Rong L. Zhai, Yun S. Xue, Ting Liang, Jia J. Mi, Zhou Xu
A direct regioselective functionalization of arenes and heteroarenes using N-alkenoxypyridinium salts as electrophilic alkylating agents for the synthesis of α-aryl/heteroaryl ketones has been developed. The method generates alkylating agents from alkynes and N-pyridine oxide followed by site-selective electrophilic substitution with a broad range of arenes and heteroarenes including benzene derivates, phenols, ethers, indoles, pyrroles, furans, and thiophenes in one pot. Kinetic isotope effect measurements and DFT studies reveal that this reaction likely proceeds through a carbon-cation intermediate.
carbon-cationpyridine oxidefuranRegioselective Areneregioselective functionalizationpyrrolealkyneetherindoleproceedthiopheneelectrophilic alkylating agentsheteroarenephenolsite-selective electrophilic substitutionElectrophilic Alkylating AgentsmethodSynthesibenzene derivatesalkenoxypyridinium saltsKetoneArylalkylating agentsKinetic isotope effect measurementsα-Heteroarene FunctionalizationketonearylsynthesisDFT studiesAlkenoxypyridinium