Synthesis of beta-functionalized porphyrins via palladium-catalyzed carbon-heteroatom bond formations: expedient entry into beta-chiral porphyrins.
A procedure was developed for the preparation of beta-monobromo-tetraphenylporphyrin (BrTPP) in a greatly improved yield from the selective bromination of tetraphenylporphyrin (TPP) by NBS. BrTPP was successfully employed as a versatile synthon for convenient synthesis of a wide range of beta-monofunctionalized porphyrins with various heteroatom functionalities via palladium-mediated carbon-heteroatom bond formations. Examples include beta-amino, -amido, -oxo, and -mercaptoporphyrins from reactions with amines, amides, alcohols, and thiols, respectively. Applying the synthetic approach to chiral amides, beta-chiral porphyrins were effectively constructed.
Gao
Guang-Yao
GY
Department of Chemistry, University of South Florida, Tampa, FL 33620-5250, USA.
Ruppel
Joshua V
JV
Allen
D Brett
DB
Chen
Ying
Y
Zhang
X Peter
XP
D000438:Alcohols / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D008956:Models, Chemical; D010165:Palladium / Q000737:chemistry*; D011166:Porphyrins / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry
D000438:Alcohols; D000577:Amides; D000588:Amines; D011166:Porphyrins; D013438:Sulfhydryl Compounds; C409084:tetraphenylporphyrin; D010165:Palladium; D002244:Carbon