Journal of the American Chemical Society
Journal of the American Chemical Society
4 years ago

Intramolecular Crossed [2+2] Photocycloaddition through Visible Light-Induced Energy Transfer

Intramolecular Crossed [2+2] Photocycloaddition through Visible Light-Induced Energy Transfer
Zhongyue Yang, K. N. Houk, Qingxuan Tang, Jiannan Zhao, Ohyun Kwon, Jonathan L. Brosmer, Paula L. Diaconescu
Herein, we present the intramolecular [2+2] cycloadditions of dienones promoted through sensitization, using a polypyridyl iridium(III) catalyst, to form bridged cyclobutanes. In contrast to previous examples of straight [2+2] cycloadditions, these efficient crossed additions were achieved under irradiation with visible light. The reactions delivered desired bridged benzobicycloheptanone products with excellent regioselectivity in high yields (up to 96%). This process is superior to previous syntheses of benzobicyclo[3.1.1]heptanones, which are readily converted to B-norbenzomorphan analogues of biological significance. Electrochemical, computational, and spectroscopic studies substantiated the mechanism of triplet energy transfer and explained the unusual regiocontrol.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b05277

DOI: 10.1021/jacs.7b05277

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