Conversion of Ni(II)-allylporphyrins to alpha,beta-unsaturated formylporphyrins via a nickel-promoted reaction.
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.
Horn
Sabine
S
School of Chemistry, SFI Tetrapyrrole Laboratory, Trinity College Dublin, Dublin 2, Ireland.
Sergeeva
Natalia N
NN
Senge
Mathias O
MO
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*
D005561:Formates; D011166:Porphyrins; C030544:formic acid; D009532:Nickel