Pd(OAc)2-catalyzed orthogonal synthesis of 2-hydroxybenzoates and substituted cyclohexanones from acyclic unsaturated 1,3-carbonyl compounds |
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| Authors: | Toshinori Miyagi Sho Okada Naoya Tada Masahiro Sugihara Natsuko Kagawa Tetsuhiko Takabatake Masahiro Toyota |
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| Institution: | 1. Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan;2. Center for Environment, Health and Field Science, Chiba University, 6-2-1 Kashiwa-no-ha, Kashiwa, Chiba 277-0882, Japan;3. Advanced Materials Development Laboratory, Sumitomo Chemical Co., Ltd., 1-98, Kasugadenaka, 3-chome, Konohana-ku, Osaka, 554-8558, Japan |
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| Abstract: | A Pd-catalyzed orthogonal synthesis of substituted 2-hydroxybenzoates and substituted cyclohexanones was developed for the first time. The substituted 2-hydroxybenzoates were obtained from acyclic unsaturated 1,3-carbonyl compounds using a combination of catalytic Pd(OAc)2 and Cu(OAc)2. On the other hand, the substituted cyclohexanones were produced from similar substrates via catalytic Pd(OAc)2 and hydrogen chloride. Each transformation was clean, easy to work up, provided the desired compounds in good purities, and did not require column chromatography purification. |
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| Keywords: | Corresponding author Palladium acetate Orthogonal synthesis 2-Hydroxybenzoate Substituted cyclohexanone |
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