T.-M. Chao, Zhe-Hong Su, Ko-Wang Yen
Mar 25, 2020
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0
Influential Citations
3
Citations
Journal
The Journal of organic chemistry
Abstract
A facile and efficient synthetic methodology for preparing dibenzosuberones via C-H bond activation strategy is presented. The ortho-aroylated 3,5-diarylisoxazole was employed as the starting substrate to undergo the palladium-catalyzed intramolecular C-H/C-Br bond cross-coupling to produce a variety of dibenzosuberones bearing an isoxazole group in 24% to > 99% 1H NMR yields. The dibenzosuberone structure was further confirmed by X-ray crystallography. The developed methodology owns very good functional group tolerance. In addition, a rational mechanism was presented for describing the reaction process. Toward the prepared dibenzosuberone, the use of Mo(CO)6 as the catalyst can easily transform the isoxazole ring into the β-aminoenone group. Finally, the structure of the anticipated ring-opening product, dibenzosuberenone bearing a β-amino-α-ketone group was secured by X-ray crystallography.