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.
Sequential Strategies to Trigger Mild Dearomative Diels-Alder Cyclizations / Camedda, N.; Bigi, F.; Maggi, R.; Maestri, G.. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 25:13(2023), pp. 2233-2237. [10.1021/acs.orglett.3c00454]
Sequential Strategies to Trigger Mild Dearomative Diels-Alder Cyclizations
Camedda N.;Bigi F.;Maggi R.;Maestri G.
2023-01-01
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.