Efficient palladium-catalyzed double carbonylation of o-dibromobenzenes: synthesis of thalidomide.
We describe here a convenient and mild procedure for double carbonylation of o-dibromobenzenes with various 2-amino pyridines and naturally occurring amines, thus providing in good to excellent yields N-substituted phthalimides by using this palladium-catalyzed carbonylation procedure. Furthermore, for the first time we have applied the developed synthetic protocol for the synthesis of biologically active molecule thalidomide via a single step carbonylative cyclization reaction in excellent yield.
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock, Germany. xiao-feng.wu@catalysis.de.
Jianbin
J
Chen
Kishore
K
Natte
Anke
A
Spannenberg
Helfried
H
Neumann
Matthias
M
Beller
Xiao-Feng
XF
Wu
D000588:Amines / Q000737:chemistry; D001969:Bromobenzenes / Q000737:chemistry*; D002384:Catalysis; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry*; D010797:Phthalimides / Q000138:chemical synthesis / Q000737:chemistry; D013792:Thalidomide / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D001969:Bromobenzenes; D010797:Phthalimides; D013792:Thalidomide; C102879:1,2-dibromobenzene; D010165:Palladium