Divergent cyclodimerizations of styrylnaphthols under aerobic visible-light irradiation and Brønsted acid catalysis - Archive ouverte HAL
Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2022

Divergent cyclodimerizations of styrylnaphthols under aerobic visible-light irradiation and Brønsted acid catalysis

Résumé

Dimeric cyclization reactions show great potential to rapidly form highly substituted complex cyclic molecules from simple starting materials. However, such an appealing process is often hampered by the lack of selectivity. Herein we report two divergent cyclodimerization reactions of 1-styrylnaphthalen-2-ol derivatives under simple and very mild reaction conditions. A stereoselective visible light-induced oxidative (1 + 1 + 4 + 4) homodimerization gave rise to highly substituted 1,5-dioxocanes in moderate yields. This transformation harnessed singlet oxygen as a safe and mild oxidant under photocatalyst-free reaction conditions. Additionally, we demonstrated that the same substrates undergo a (4 + 2) heterodimerization under Brønsted-acid catalysis to produce chromane derivatives featuring 3 contiguous tertiary stereocenters in good to high yields with excellent diastereoselectivities.

Domaines

Chimie organique
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Dates et versions

hal-04295816 , version 1 (08-11-2023)
hal-04295816 , version 2 (20-11-2023)

Identifiants

Citer

Jiyuan Lyu, Aurélie Claraz, Pascal Retailleau, Géraldine Masson. Divergent cyclodimerizations of styrylnaphthols under aerobic visible-light irradiation and Brønsted acid catalysis. Organic & Biomolecular Chemistry, 2022, 20 (48), pp.9593-9599. ⟨10.1039/D2OB01509A⟩. ⟨hal-04295816v1⟩
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