Premium
A Palladium‐Catalyzed Double Carbonylation Approach to Isatins from 2‐Iodoanilines
Author(s) -
Laursen Simon R.,
Jensen Mikkel T.,
Lindhardt Anders T.,
Jacobsen Mikkel F.,
Skrydstrup Troels
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600143
Subject(s) - chemistry , carbonylation , palladium , catalysis , organic chemistry , combinatorial chemistry , carbon monoxide
Abstract A high‐yielding procedure for the synthesis of isatins has been developed. Sequential Pd‐catalyzed double carbonylation of 2‐iodoanilines with near stoichiometric amounts of CO followed by acid‐promoted cyclization readily affords an array of isatins. The conversion of 2‐iodoanilines to isatins in good to excellent yields was found to proceed with good functional group tolerance. This protocol proved adaptable to 13 C‐isotope labeling of isatins, which was extended to the synthesis of the 13 C‐isotope labeled antiviral drug metisazone and the experimental anti‐schizophrenia drug ML137.