中文摘要
在實驗過二十四種不同的氧金屬催化劑後，發現對於親核性醯基取代反應上，三氟甲磺酸氧釩（VO(OTf)2）、正六價二氯化雙氧鉬 （MoO2Cl2）和正六價四氯化氧鉬（MoOCl4）三者為最有效的催化劑。針對一系列的親核試劑如醇類、胺類以及硫醇類來說，上述的催化劑可以達到高化學產率以及高化學官能基的選擇性。眾所週知，氧鉬金屬對於氧化反應已有完整的研究。然而，對於親核性醯基取代反應而言，氧鉬金屬催化劑在具有多種官能基團的化學環境裡仍保有高安定的特性則是催化反應中空前的新發現。
我們進一步利用苯甲酸酐為媒介，針對各種官能基化的酸類化合物生成混合酸酐，可以將親核試劑進一步修飾為油酸酯（oleate）， 雙肽（dipeptide），雙苯基甲基衍生物（diphenylmethyl），N-9茀甲氧羰基-α-胺基酸衍生物（N-Fmoc-α-amino），丙酮醯基衍生物（pyruvic），第三丁基硫酯衍生物（tert-butylthio ester），第三丁基醯胺衍生物（N-tert-butylamide）和三芳香基甲基衍生的丙烯醯基酯類（trityl acrylate）等官能化產物。另一方面，我們利用核磁共振光譜（NMR）與電灑式質譜儀（ESI-MS）的動力學實驗得知，在親核性醯基取代反應上，相較於之前本實驗室所發表的氧釩金屬催化劑而言，鉬和釩兩金屬對於氧金屬中心的兩性特質與行為具有高度的相似性。

英文摘要
Among twenty-four different oxo-metallic species examined, vanadyl triflate, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. The catalytic NAS tolerates virtually all kinds of functional groups and was unprecedented in view of the well-recognized redox chemical behaviors associated with oxomolybdenum (VI) species. By using benzoic anhydride as a mediator for in-situ generation of an incipient mixed-anhydride with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-α-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide and trityl acrylate syntheses with appropriate protic nucleophiles. Similar to vanadyl species, the amphoteric character of the Mo=O unit in oxomolybdenum chlorides was proven by 1H NMR kinetic experiments to be responsible for the catalytic NAS profile.

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(64) See the Supporting Information for details.
(65) Pivalations did not work properly due to the poor solubility of these substrates in pivalic anhydride.
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(67) Unpublished results from this laboratory.
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