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Intermolecular [2+2] photocycloaddition of chalcones with 2,3-dimethyl-1,3-butadiene under neat reaction conditions

Author:
Tang, Fang, Tang, Li, Guan, Zhi, He, Yan-Hong
Source:
Tetrahedron 2018 v.74 no.46 pp. 6694-6703
ISSN:
0040-4020
Subject:
additives, catalysts, chalcones, chemical structure, cycloaddition reactions, density functional theory, irradiation, photosensitizing agents, regioselectivity, solvents, stereoselectivity
Abstract:
The intermolecular [2 + 2] photocycloaddition of chalcones with 2,3-dimethyl-1,3-butadiene under visible-light irradiation for the synthesis of cyclobutane derivatives has been developed. Without using any photosensitizer, metallic catalyst and solvent, the reaction proceeded with high regioselectivity and moderate to high stereoselectivity. Mild reaction conditions and no additives make the reaction easy to operate. Control experiments and density functional theory (DFT) computations demonstrated that the reaction takes place via visible-light activation of chalcones, which is different from the previously reported [2 + 2] cycloaddition of chalcones.
Agid:
6159635