Process for preparing biphenyls using palladacycles as catalysts

US5559277A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Matthias Beller · Ostseebad Nienhagen, DE
• Wolfgang Anton Herrmann · Freising, DE
• Christoph Brossmer · Frankfurt, DE

Key dates

• Filing date: Jun 29, 1995
• Grant date: Sep 24, 1996
• Expiry date: Jun 29, 2015

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C49/784
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

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 fo…