Process for preparing biphenyls using palladacycles as catalysts

Details Process for preparing biphenyls using palladacycles as catalysts Process for preparing biphenyls using palladacycles as catalysts

1995-06-29

1996-09-24

Caldarola, Glenn A.

Chemistry of hydrocarbon compounds

Aromatic compound synthesis

From nonhydrocarbon feed

585457, 570190, C07C25550, C07C25330, C07C 132

Patent

active

055592775

ABSTRACT:
The invention relates to a process for preparing biphenyls of the formula (I) ##STR1## where R.sup.1a to R.sup.10a are, independently of one another, hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.12 -alkenyl, C.sub.1 -C.sub.12 -alkynyl, alkoxy-(C.sub.1 -C.sub.12), acyloxy-(C.sub.1 -C.sub.12), O-phenyl, aryl, heteroaryl, fluorine, chlorine, OH, NO.sub.2, CN, COOH, CHO, SO.sub.3 H, SO.sub.2 R, SOR, NH.sub.2, NH-alkyl-(C.sub.1 -C.sub.12), N-alkyl.sub.2 -(C.sub.1 -C.sub.12), C-Hal.sub.3, NHCO-alkyl-(C.sub.1 -C.sub.8), CONH-alkyl-(C.sub.1 -C.sub.4), CON-(alkyl).sub.2 -(C.sub.1 -C.sub.4), COO-alkyl-(C.sub.1 -C.sub.12), CONH.sub.2, CO-alkyl-(C.sub.1 -C.sub.12), NHCOH, NHCOO-alkyl-(C.sub.1 -C.sub.8), CO-phenyl, COO-phenyl, CHCHCO.sub.2 -alkyl-(C.sub.1 -C.sub.12), CHCHCO.sub.2 H, PO-phenyl.sub.2, PO-alkyl.sub.2 -(C.sub.1 -C.sub.8), by reaction of haloaromatics or aryl sulfonates of the formula (II) ##STR2## with arylboron derivatives of the formula III ##STR3## where R.sup.1a to R.sup.10a are as defined above and X is bromine, chlorine or OSO.sub.2 CF.sub.3, OSO.sub.2 -aryl, OSO.sub.2 -alkyl and Y is B(OH).sub.2, B(O-alkyl).sub.2, B(O-aryl).sub.2, wherein a palladium compound of the formula (IV) ##STR4## 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.5 -C.sub.8)-cycloalkyl, (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, is used as catalyst.

REFERENCES:
patent: 4294976 (1981-10-01), Itatanu et al.
patent: 5130439 (1992-07-01), Lo et al.
patent: 5159082 (1992-10-01), Sato et al.
patent: 5254776 (1993-10-01), Lang et al.
patent: 5451703 (1995-09-01), Schach et al.

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