高钌酸四正丙基铵

高钌酸四正丙基铵
	IUPAC名; Tetrapropylammonium perruthenate
别名	四正丙基高钌酸铵; 四丙基高钌酸铵; 高钌酸四丙基铵; 过钌酸四丙铵
识别
缩写	TPAP; TPAPR
CAS号	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
性质
化学式	C12H28NRuO4
摩尔质量	351.43 g·mol⁻¹
外观	绿色固体
熔点	160 °C（433 K）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

高钌酸四正丙基铵（缩写TPAP或TPAPR）是一种化合物，化学式为N(C₃H₇)₄RuO₄，有时被称作Ley–Griffith试剂，用于有机合成。它是离子化合物，氧化性很强，但是其单电子还原的衍生物是用于将醇转化为醛的温和氧化剂。^[1]该氧化剂也可用于将伯醇直接氧化至羧酸。使用较高的催化剂负载量，较大量的助氧化剂，以及两当量的水。在这种情况下，醛与水反应形成偕二醇水合物，然后再次被氧化。^[2]

氧化反应产生水，可以通过分子筛去除。TPAP价格昂贵，但它可以以催化量使用。通过加入化学计量比的助氧化剂（如N-甲基吗啉-N-氧化物）^[3]或氧气^[4]来维持催化循环。

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

参考文献

^ 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. （原始内容存档 (PDF)于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. （原始内容存档 (PDF)于2017-08-09）.

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