Synthesis of Tetrahydrofurans and Pyrrolidines by Copper-Catalyzed Oxy/Aminoarylation of Alkenes.
Yohann LandrainGwilherm EvanoPublished in: Organic letters (2023)
An efficient copper-catalyzed inter/intramolecular oxy/aminoarylation of γ-hydroxy/aminoalkenes with diaryliodonium triflates is reported. Simple activation of these arylating agents with copper(II) triflate in dichloromethane triggers a smooth activation of the alkene, which is simultaneously trapped by the internal nucleophile, yielding, depending upon its nature, a range of highly substituted tetrahydrofurans and pyrrolidines. The cyclization was moreover found to be stereospecific, with diastereoisomeric alkenes yielding diastereoisomers of the cyclized product, and could be extended to oxyalkynylation.
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