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Tris(2,4,6-trimethoxyphenyl)phosphine

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Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP) is a large triaryl organophosphine whose strong Lewis-basic properties make it useful as an organocatalyst for several types of chemical reactions.

Tris(2,4,6-trimethoxyphenyl)phosphine
Names
IUPAC name
Tris(2,4,6-trimethoxyphenyl)phosphane
Other names
  • Tris(2,4,6-trimethoxyphenyl)phosphine
  • TTMPP
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 811-745-3
  • InChI=1S/C27H33O9P/c1-28-16-10-19(31-4)25(20(11-16)32-5)37(26-21(33-6)12-17(29-2)13-22(26)34-7)27-23(35-8)14-18(30-3)15-24(27)36-9/h10-15H,1-9H3
    Key: JQKHNBQZGUKYPX-UHFFFAOYSA-N
  • COC1=CC(=C(C(=C1)OC)P(C2=C(C=C(C=C2OC)OC)OC)C3=C(C=C(C=C3OC)OC)OC)OC
Properties
C27H33O9P
Molar mass 532.526 g·mol−1
Melting point 79–81 °C (174–178 °F; 352–354 K)
Boiling point 360 or 377 °C (680 or 711 °F; 633 or 650 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Reactions

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TTMPP removes the trimethylsilyl group from ketene silyl acetals (the enol ether of esters) to give enolates that can then act as strong nucleophiles. It thus serves as a catalyst for Mukaiyama aldol reactions[2] and group-transfer chain-growth polymerization reactions.[3]

As a Brønsted base, TTMPP can deprotonate various alcohols, giving nucleophilic alkoxides that can undergo Michael addition reactions.[4]

TTMPP can act as a Michael nucleophile itself to catalyze Baylis–Hillman reactions.[5]

Uses

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TTMPP is used as a ligand to form palladium-phosphine catalysts which are more reactive than triphenylphosphine-based catalysts.[6]

References

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  1. ^ Various chemical catalogs give one or the other value (see ChemSpider for collected list)
  2. ^ Matsukawa, Satoru; Okano, Naoko; Imamoto, Tsuneo (2000). "Phosphine catalyzed aldol reaction between ketene silyl acetals and aldehydes: nucleophilic O–Si and C–Si bond cleavage by phosphines". Tetrahedron Letters. 41 (1): 103–107. doi:10.1016/S0040-4039(99)02014-6.
  3. ^ Fevre, Maréva; Vignolle, Joan; Heroguez, Valérie; Taton, Daniel (2012). "Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP) as Potent Organocatalyst for Group Transfer Polymerization of Alkyl (Meth)acrylates". Macromolecules. 45 (19): 7711–7718. Bibcode:2012MaMol..45.7711F. doi:10.1021/ma301412z.
  4. ^ Fischer, Susanne M.; Kaschnitz, Petra; Slugov, Christian (2022). "Tris(2,4,6-trimethoxyphenyl)phosphine – a Lewis base able to compete with phosphazene bases in catalysing oxa-Michael reactions". Catalysis Science & Technology. 12 (20): 6204–6212. doi:10.1039/D2CY01335E.
  5. ^ Trofimov, Alexander; Gevorgyan, Vladimir (2009). "Sila-Morita−Baylis−Hillman Reaction of Arylvinyl Ketones: Overcoming the Dimerization Problem". Organic Letters. 11 (1): 253–255. doi:10.1021/ol8026522. PMID 19055398.
  6. ^ Miyaura, Norio; Suzuki, Akira (1995). "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds". Chemical Reviews. 95 (7): 2457–2483. doi:10.1021/cr00039a007. hdl:2115/44007.
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