One-pot synthesis of meso-formylporphyrins by S(N)Ar reaction of 5,15-disubstituted porphyrins with (2-pyridyldimethylsilyl)methyllithium.
A simple, one-pot procedure that converts 5,15-substituted porphyrins into the corresponding meso-formylated porphyrins has been developed. The method, based on a new synthetic concept for functionalized porphyrins utilizing the (2-pyridyldimethylsilyl)methyl group as a latent formyl functionality, affords the desired product in good yield and is especially appropriate for the direct formylation of free base porphyrins, which has never been achieved by known methods.
Takanami
Toshikatsu
T
Meiji Pharmaceutical University, Noshio, Kiyose, Tokyo 204-8588, Japan. takanami@my-pharm.ac.jp
Wakita
Atsushi
A
Sawaizumi
Aoyo
A
Iso
Kazuhiro
K
Onodera
Hidetoshi
H
Suda
Kohji
K
D002384:Catalysis; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
D009942:Organometallic Compounds; D011166:Porphyrins; D008094:Lithium; D012825:Silicon