Water Soluble Cationic Phosphine Ligands Containing <i>m</i>-Guanidinium Phenyl Moieties. Syntheses and Applications in Aqueous Heck Type Reactions
作者:Antonella Hessler、Othmar Stelzer、Harald Dibowski、Karin Worm、Franz P. Schmidtchen
DOI:10.1021/jo961140n
日期:1997.4.1
Cationic phosphine ligands containing m-guanidinium phenyl substituents Ph(3-n)P[C(6)H(4)-m-NHC(NH(2))(NMe(2))](n)}(n+) nCl(-) (n = 1-3) (17a-c) have been obtained by addition of dimethylcyanamide to the amino groups of tertiary (m-aminophenyl)phosphines in acidic medium. The tertiary (m-aminophenyl)phosphines Ph(3-n)P(C(6)H(4)-m-NH(2))(n) (4a-c) were prepared by reaction of (3-[N,N-bis(trimethyl
包含间胍基苯基取代基的阳离子膦配体Ph(3-n)P [C(6)H(4)-m-NHC(NH(2))(NMe(2))](n)}(n +) nCl(-)(n = 1-3)(17a-c)是通过在酸性介质中将二甲基氰胺加到叔(间氨基苯基)膦的氨基上而获得的。叔(间氨基苯基)膦Ph(3-n)P(C(6)H(4)-m-NH(2))(n)(4a-c)通过(3- [N ,N-双(三甲基甲硅烷基)氨基]苯基)氯化镁与氯膦Ph(3-n)PCl(n),然后用甲醇对双(三甲基甲硅烷基)氨基进行脱保护。使用与上述类似的保护基合成方法,也可以制备仲(间氨基苯基)膦Ph(H)PC(6)H(4)-m-NH(2)(7)。它可以用作合成带有间氨基苯基取代基的手性二齿膦配体(11、14和15)的基础。胍鎓膦17b和17c易溶于水。钯催化水相中17b和17c,芳基烷基胍鎓膦18和19和TPPTS(P(C(6)H(4)-m-SO(