Process for preparing aromatic acetylenes using palladacycles as

Details Process for preparing aromatic acetylenes using palladacycles as Process for preparing aromatic acetylenes using palladacycles as

1996-04-26

1999-03-23

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568780, 568939, 568795, 556136, C07C 3702

Patent

active

058862404

ABSTRACT:
The invention relates to a process for preparing aromatic acetylenes of the formula (I): Ar--C.tbd.C--R.sup.8a, where Ar is: ##STR1## by reacting haloaromatics or aryl sulfonates of the formula (II): Ar--X, with monosubstituted acetylenes of the formula (III): Ar--C.tbd.C--R.sup.8a, where Ar is defined above and X is bromine, chlorine or OSO.sub.2 R, in the presence of a palladium compound catalyst of the formula (IV): ##STR2## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 are, independently of one another, hydrogen (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, fluorine, NH.sub.2, NH-alkyl-(C.sub.1 -C.sub.4), N(alkyl).sub.2 -(C.sub.1 -C.sub.4), CO.sub.2 -alkyl-(C.sub.1 -C.sub.4), OCO-alkyl-(C.sub.1 -C.sub.4), or phenyl, or R.sup.1 and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.5 and R.sup.6, together form an aliphatic or aromatic ring, and R.sup.7, R.sup.8 are (C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.12)-cycloalkyl, substituted or unsubstituted aryl, and Y is an anion of an inorganic or organic acid.

REFERENCES:
patent: 3632824 (1972-01-01), Fitton
patent: 4128588 (1978-12-01), Sabourin
J. Org. Chem, Mitsudo, vol. 49, pp. 1640-1646, 1984.
March "Advanced Organic Chemistry" 1968 p. 552.
CA 100:209245 -Abst. of J. Organ Chem "Palladiumcatalyzed syntheses of aryl polyenes" 1984.
J. Mol. Catal. A: Chem; vol. 108; pp. 51-56; Herrmann W A et al: "Coordination chemistry and mechanisms of metal-catalyzed C-C coupling reactions. Part 8. Facile catalytic coupling of aryl bromides with terminal alkynes by phospha-palladacycles".
Bulletin of The Academy of Sciences of the USSR Division of Chemical Science., Bd. 37, Nr. 3, 1988, New York, US, pp. 507-509; N.A. Bumagin et al: "Reactions of terminal acetylenes with aryl iodides catalyzed by palladium complexes under interfacial conditions".
Dieck, H. A., et al, J. of Organometallic Chem. 93: 259-263 (1975).

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