Three-component coupling of acylphosphonates and two carbonyl compounds promoted by low-valent samariums: one-Pot synthesis of beta-hydroxyphosphonates |
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| Authors: | Takaki Itono Nagafuji Naito Shishido Takehira Makioka Taniguchi Fujiwara |
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| Affiliation: | Department of Applied Chemistry, Faculty of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527, Japan, and Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Hakozaki, Fuku. |
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| Abstract: | Three-component coupling of acylphosphonates and two carbonyl compounds leading to beta-hydroxyphosphonates has been achieved with low-valent samariums. Thus, acylphosphonates reacted with aldehydes in the presence of semicatalytic amounts of samarium metal or SmI(2) to give acyloxyphosphonates in good yields. The second coupling reaction of the acyloxyphosphonates with aldehydes or ketones promoted by SmI(2) afforded beta-hydroxyphosphonates instead of olefins. Moreover, these two reactions could be carried out in one pot. |
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