Patent ID: 6417357
Filing Date: 2002-07-09
Classification: C07B,C07C,C07D,C07F

Abstract:
A process for the preparation of a biphenyl of formula wherein A and B define substituents; m and n define integers from 0 to 5 and the number of substituents at the phenyl radicals D and E; or of an aromatic olefin of formula â€ƒwherein C defines substituents, o defines integers from 0 to 5 and the number of substituents at the phenyl radical F, and R6, R7 and R8 are hydrogen or substituents, which process comprises a) subjecting a phenyl derivative of formula â€ƒwherein A, B, m and n have the meanings cited for formula I and X is a leaving group, for the preparation of the biphenyl (I) to a coupling reaction with an arylboronic acid derivative of formula â€ƒwherein A, B, m and n have the meanings cited for formula I and Y is the â€”B(OH)2 group or mono- or diester derivatives of â€”B(OH)2; and b) subjecting a phenyl derivative of formula â€ƒwherein C and o have the meanings cited for formula II and X is a leaving group, for the preparation of the aromatic olefin (II) to a coupling reaction with an olefin of formula â€ƒwherein R6, R7 and R8 have the meanings cited for formula II, each in the presence of a catalytically effective amount of an olefinic palladium complex compound of formula â€ƒwherein L is a neutral ligand having electron-donor properties, Z is an anionic ligand and D is a substituent, and p is an integer from 0 to 5 and defines the number of substituents at the allyl group; or aâ€²) subjecting a phenyl derivative (III a) or (IIIb), wherein A, B, m and n have the meanings cited for formula I and X is chloro, bromo or iodo, for the preparation of the biphenyl (I) to a coupling reaction with an arylboronic acid derivative (IV a) or (IV b), wherein A, B, m and n have the meanings cited for formula I and Y is theâ€”B(OH)2 group or mono- or diester derivatives ofâ€”B(OH)2; or bâ€²) subjecting a phenyl derivative (V), wherein C and o have the meanings cited for formula II and X is bromo or iodo, for the preparation of the aromatic olefin (II) to a coupling reaction with an olefin (VI), wherein R6, R7 and R8 have the meanings cited for formula II, each in the presence of a catalytically effective amount of an olefinic ionic palladium complex compound of formula â€ƒwherein Z1 and Z2 are anionic ligands and K+ is a non-coordinating cation, and D and p have the cited meanings, and isolating the biphenyl (I) or the condensed aromatic olefin (II) after the completion of the process variants a), b), aâ€²) or bâ€²).