Selective production of aryl phosphonium salts in practically quantitative yields and with improved work up, without use of noble metal complexes or nickel-oxygen complexes as catalysts

摘要

A salt-type nickel compound is used as a catalyst for preparation of phosphonium salts of formula (I) by reaction of a substituted phosphine of formula (II) with an aryl compound of formula (III). Some compounds (I) are also new. Preparation of phosphonium salts of formula (I), or hydrates of (I), comprises: (a) reaction of a substituted phosphine of formula (II) with an aryl compound of formula (III), in a solvent, in the presence of a salt-type nickel compound, at 60-180 deg C and an absolute pressure of 10 mbar to 20 bar; and (b) isolation of (I). R (in (I)) = (i) aryl or (ii) a bridging substituent which links the phosphorus atom directly with an aromatic ring system; R (in (II)) = (i) aryl or (ii) a residue with which several groups Y are linked directly with an aromatic ring system; R1, R2, R3 = aryl, 1-20C alkyl, 3-8C cycloalkyl or optionally substituted benzyl; X- = a monovalent anion or an equivalent of a polyvalent anion; Y = Cl, Br, I or some other leaving group An Independent claim is included for phosphonium salts of formula (I'): R1, R2, R3 = aryl, 1-20C alkyl, 3-8C cycloalkyl or optionally substituted benzyl; R4, R5, R6 = Cl, Br, I, F, Q, a fused ring (e.g. 1- or 2-naphthyl or anthracenyl), a hetero-fused ring (e.g. indolyl), biphenyl, COOH, CONH2, SO3H, SO2Q, OH, SH, OQ, N(Q)2, CHO, CH=NQ, COOQ, COSQ, CONHQ or CON(Q)2; Q = a 1-20C chain which may be branched and/or unsaturated