高釕酸四正丙基銨

高釕酸四正丙基銨
	IUPAC名; Tetrapropylammonium perruthenate
別名	四正丙基高釕酸銨; 四丙基高釕酸銨; 高釕酸四丙基銨; 過釕酸四丙銨
識別
縮寫	TPAP; TPAPR
CAS號	114615-82-6
ChemSpider	21170134
SMILES	CCC[N+](CCC)(CCC)CCC.O=[Ru](=O)([O-])=O;
InChI	1/C12H28N.4O.Ru/c1-5-9-13(10-6-2,11-7-3)12-8-4;;;;;/h5-12H2,1-4H3;;;;;/q+1;;;;-1;/rC12H28N.O4Ru/c1-5-9-13(10-6-2,11-7-3)12-8-4;1-5(2,3)4/h5-12H2,1-4H3;/q+1;-1;
InChIKey	NQSIKKSFBQCBSI-DQAXOFGLAB
性質
化學式	C12H28NRuO4
莫耳質量	351.43 g·mol⁻¹
外觀	綠色固體
熔點	160 °C（433 K）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

高釕酸四正丙基銨（縮寫TPAP或TPAPR）是一種化合物，化學式為N(C₃H₇)₄RuO₄，有時被稱作Ley–Griffith試劑，用於有機合成。它是離子化合物，氧化性很強，但是其單電子還原的衍生物是用於將醇轉化為醛的溫和氧化劑。^[1]該氧化劑也可用於將伯醇直接氧化至羧酸。使用較高的催化劑負載量，較大量的助氧化劑，以及兩當量的水。在這種情況下，醛與水反應形成偕二醇水合物，然後再次被氧化。^[2]

氧化反應產生水，可以通過分子篩去除。TPAP價格昂貴，但它可以以催化量使用。通過加入化學計量比的助氧化劑（如N-甲基嗎啉-N-氧化物）^[3]或氧氣^[4]來維持催化循環。

醇至醛的氧化反應，所需TPAP（0.06 eq）、N-甲基嗎啉-N-氧化物（1.7 eq）以及二氯甲烷中的分子篩^[5]

參考文獻

^ Ley, Steven V.; Norman, Joanne; Griffith, William P.; Marsden, Stephen P. Tetrapropylammonium perruthenate, Pr₄N⁺RuO₄⁻, TPAP: A catalytic oxidant for organic synthesis. Synthesis. 1994: 639–666. doi:10.1055/s-1994-25538. (review article)
^ Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. Applications of Zr-catalyzed carbomagnesation and Mo-catalyzed macrocyclic ring closing metathesis in asymmetric synthesis. Enantioselective total synthesis of Sch 38516 (Fluvirucin B₁). J. Am. Chem. Soc. 1997, 119: 10302–10316. doi:10.1021/ja972191k.
^ Griffith, William P.; Ley, Steven V.; Whitcombe, Gwynne P.; White, Andrew D. Preparation and use of tetra-n-butylammonium per-ruthenate (TBAP reagent) and tetra-n-propylammonium per-ruthenate (TPAP reagent) as new catalytic oxidants for alcohols. J. Chem. Soc., Chem. Commun. 1987: 1625–1627. doi:10.1039/C39870001625.
^ Lenz, Roman; Ley, Steven V. Tetra-n-propylammonium perruthenate (TPAP)-catalysed oxidations of alcohols using molecular oxygen as a co-oxidant. J. Chem. Soc., Perkin Trans. 1. 1997: 3291–3292. doi:10.1039/A707339I.
^ Hadfield, John A.; McGown, Alan T.; Butler, John. A high-yielding synthesis of the naturally occurring antitumour agent irisquinone (PDF). Molecules. 2000, 5: 82–88 [2017-06-25]. doi:10.3390/50100082. （原始內容存檔 (PDF)於2017-08-09）.

[1] Ley, Steven V.; Norman, Joanne; Griffith, William P.; Marsden, Stephen P. Tetrapropylammonium perruthenate, Pr₄N⁺RuO₄⁻, TPAP: A catalytic oxidant for organic synthesis. Synthesis. 1994: 639–666. doi:10.1055/s-1994-25538. (review article)

[2] Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. Applications of Zr-catalyzed carbomagnesation and Mo-catalyzed macrocyclic ring closing metathesis in asymmetric synthesis. Enantioselective total synthesis of Sch 38516 (Fluvirucin B₁). J. Am. Chem. Soc. 1997, 119: 10302–10316. doi:10.1021/ja972191k.

[3] Griffith, William P.; Ley, Steven V.; Whitcombe, Gwynne P.; White, Andrew D. Preparation and use of tetra-n-butylammonium per-ruthenate (TBAP reagent) and tetra-n-propylammonium per-ruthenate (TPAP reagent) as new catalytic oxidants for alcohols. J. Chem. Soc., Chem. Commun. 1987: 1625–1627. doi:10.1039/C39870001625.

[4] Lenz, Roman; Ley, Steven V. Tetra-n-propylammonium perruthenate (TPAP)-catalysed oxidations of alcohols using molecular oxygen as a co-oxidant. J. Chem. Soc., Perkin Trans. 1. 1997: 3291–3292. doi:10.1039/A707339I.

[5] Hadfield, John A.; McGown, Alan T.; Butler, John. A high-yielding synthesis of the naturally occurring antitumour agent irisquinone (PDF). Molecules. 2000, 5: 82–88 [2017-06-25]. doi:10.3390/50100082. （原始內容存檔 (PDF)於2017-08-09）.

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