New Heck-type reaction applied to the synthesis of protoporphyrin-IX derivatives.
[reaction: se text] A new Heck-type reaction under catalysis by Pd for obtaining polysubstituted arylvinylydene derivatives of porphyrin systems is reported. The coupling between the Zn(II)-protoporphyrin-IX dimethylester Zn-2 and several bromo-aryl and iodo-aryl compounds in the presence of a new Pd catalyst has been studied. This coupling reaction, although providing moderate regioselectivity, gives quantitative conversion.
Castella
M
M
Departament de Química Orgànica and Departament de Química Inorgànica, Universitat de Barcelona, Martí i Franqués 1-11, E-08028 Barcelona, Catalunya, Spain.
Calahorra
F
F
Sainz
D
D
Velasco
D
D
D002384:Catalysis; D002855:Chromatography, Thin Layer; D006427:Hemin / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D008665:Metalloporphyrins / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium; D011166:Porphyrins; D011524:Protoporphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry; D015032:Zinc
D006846:Hydrocarbons, Halogenated; D008665:Metalloporphyrins; D011166:Porphyrins; D011524:Protoporphyrins; D014753:Vinyl Compounds; D010165:Palladium; D006427:Hemin; C028025:protoporphyrin IX; D015032:Zinc