[69073-98-9]  · C46H48O4P2Pd  · Diacetatobis(tri-o-tolylphosphine)palladium(II)  · (MW 833.25)

(catalyst for coupling of aromatic halides and alkenes;1-3 cycloisomerization reactions of enynes4)

Alternate Name: bis(tri-o-tolylphosphine)palladium(II) diacetate.

Solubility: sol acetonitrile, DMF, halogenated solvents.

Preparative Method: usually generated in situ from Palladium(II) Acetate and tri-o-tolylphosphine and used directly.

Handling, Storage, and Precautions: air sensitive in solution.

Coupling of Aryl Halides with Alkenes.

The title reagent (1) has been used to make aromatic alkenes in good yield under mild conditions, tolerating a variety of functionality (eq 1). Aromatic bromides2 and iodides3 are coupled with alkenes in the presence of base (typically NEt3) in refluxing acetonitrile or DMF.

This reaction can be used to produce aromatic polymers.5 In many cases, (1) is superior to the triphenylphosphine analog1 (see Bis(triphenylphosphine)palladium(II) Acetate).


Pd{P(o-Tol)3}2(OAc)2 will readily effect cycloisomerization of 1,6-enyne substrates to 1,3-dienes,4,6 and has been used in the synthesis of sterepolide (eq 2).7

1. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic: London, 1987.
2. Spencer, A. JOM 1984, 265, 323.
3. Bender, D. D.; Stakem, G.; Heck, R. F. JOC 1982, 47, 1278.
4. Trost, B. M. ACR 1990, 23, 34.
5. Suzuki, M.; Lim, J.-C.; Saegusa, T. Macromolecules 1990, 23, 1574.
6. Trost, B. M; Lautens, M. JACS 1985, 107, 1781.
7. (a) Trost, B. M.; Hipskind, P. A.; Chung, J. Y. L.; Chan, C; AG 1989, 101, 1559; (b) Trost, B. M; Chung, J. Y. L. JACS 1985, 107, 4586.

Anthony Fulford

Johnson Matthey, Royston, UK

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