Tris(2,4,6-trimethoxyphenyl)phosphine explained

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.

Reactions

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[1] and group-transfer chain-growth polymerization reactions.[2]

As a Brønsted base, TTMPP can deprotonate various alcohols, giving nucleophilic alkoxides that can undergo Michael addition reactions.[3]

TTMPP can act as a Michael nucleophile itself to catalyze Baylis–Hillman reactions.[4]

Uses

TTMPP is used as a ligand to form palladium-phosphine catalysts which are more reactive than triphenylphosphine-based catalysts.[5]

Notes and References

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

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