Arylamine preparation in high yield, for use as intermediate for e.g. drugs or pesticides, from aryl halide and aniline or diphenylamine derivative over catalyst comprising palladium compound and tris-(silyl)-phosphine

摘要

The preparation of arylamines (I) by reacting a halogenated phenyl, biphenyl, bis-phenyl or triphenylamine compound (II) with an aniline or diphenylamine derivative (III), in presence of base, is catalyzed by a palladium compound and a tris-(tri-substituted silyl)-phosphine (IV). Preparation of arylamines (I) involves reacting a halo-aryl compound (II) of formula (IIA)-(IIC) with an aniline or diphenylamine derivative (III) of formula (IIIA) or (IIIB) in presence of an organic or inorganic base and a catalyst consisting of a palladium compound and a tris-(silyl)-phosphine of formula (IV): R10-R24 = halo (at least one of R10-R24 in (IIA)-(IIC) being halo, preferably Br or I); H; CN; 1-20C (preferably 1-6C) alkyl, 1-20C (preferably 1-6C) alkoxy, 3-20C (preferably 5-10C) cycloalkyl, aryl (such as optionally substituted phenyl (preferably o-substituted phenyl such as 2,3-dimethylphenyl or mesityl), naphthyl or higher fused systems such as anthracenyl, phenanthrenyl or pyrenyl), aralkyl (such as benzyl or (1-methylethyl)-phenyl (sic)), dialkylamino, alkyl-aryl-amino, aralkylamino or diarylamino (all optionally substituted by groups such as alkoxy, dialkylamino, aryloxy, aryl-alkylamino or diarylamino, themselves optionally substituted by other groups as for R10-R24); or vinyl (optionally substituted by other groups as for R10-R24); or R10-R24 = parts of rings (possibly connecting different aryl rings); Am = direct bond, O or S; or 1-20C alkylene (such as CH2, CH2CH2 or (CH2)3), vinylene, arylene (such as 1,4-phenylene or 4,4'-biphenylene) or N (all optionally substituted by groups as for R10-R24); R1-R9 = 1-20C (preferably 1-6C) alkyl, 3-20C (preferably 5-10C) cycloalkyl, aryl (such as phenyl, naphthyl or higher fused systems such as anthracenyl, phenanthrenyl or pyrenyl), aralkyl (such as benzyl or (1-methylethyl)-phenyl (sic)); or R1-R9 = parts of rings, connecting R1-R3, R4-R6 or R7-R9 or bridging R1 and R9, R3/R4 and/or R6/R7.