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Sequential Strategies to Trigger Mild Dearomative Diels-Alder Cyclizations
Nicola Camedda1, Franca Bigi1,2, Raimondo Maggi1
1Università di Parma, Department of Chemistry, Life Sciences and Environmental Sustainability, Parco Area delle Scienze 17/A, 43124 Parma, Italy.
Abstract:
Dihydronaphthalenes are present in several functional molecules, but their assembly is challenging. However, a sequential strategy can induce the key annullation of an alkyne with a vinylarene under mild conditions. Products form in good yields, with ample functional tolerance via domino nucleophilic substitution and dearomative Diels-Alder and ene reactions. DFT modeling data show that alkali cations are crucial to ensure a smooth dearomative cyclization on the in situ generated intermediates.
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