Expedient drug synthesis and diversification via ortho-C-H iodination using recyclable PdI2 as the precatalyst.
Pd(II)-catalyzed ortho-C-H iodination reactions of phenylacetic acid substrates have been achieved using recyclable PdI(2) as the precatalyst. This class of substrates is incompatible with the classic amide formation/ortho-lithiation/iodination sequence. The power of this new technology is demonstrated by facile drug functionalization and drastically shortened syntheses of the drugs diclofenac and lumiracoxib.
Mei
Tian-Sheng
TS
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Wang
Dong-Hui
DH
Yu
Jin-Quan
JQ
D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D006859:Hydrogen / Q000737:chemistry*; D007700:Kinetics; D010165:Palladium / Q000737:chemistry*; D010648:Phenylacetates / Q000737:chemistry; D011522:Protons
D010648:Phenylacetates; D011522:Protons; D010165:Palladium; D002244:Carbon; D006859:Hydrogen; C025136:phenylacetic acid