title: Conversion of Ni(II)-allylporphyrins to alpha,beta-unsaturated formylporphyrins via a nickel-promoted reaction.
abstract: A new route to alpha,beta-unsaturated formylporphyrins begins with the synthesis of allyl-substituted porphyrins via the Suzuki cross-coupling reaction of bromoporphyrins and allylboronic acid pinacol ester in 50-95% yield. Treatment of allyl-substituted porphyrins with nickel acetate in N,N-dimethylformamide (DMF) then affords mono- and diacroleinylporphyrins in up to 70% yield.
authors.affiliation: School of Chemistry, SFI Tetrapyrrole Laboratory, Trinity College Dublin, Dublin 2, Ireland.
authors.forename: Sabine
authors.initials: S
authors.lastname: Horn
authors.forename: Natalia N
authors.initials: NN
authors.lastname: Sergeeva
authors.forename: Mathias O
authors.initials: MO
authors.lastname: Senge
mesh_terms: D018360:Crystallography, X-Ray; D005561:Formates / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D005561:Formates; D011166:Porphyrins; C030544:formic acid; D009532:Nickel