Hartwig-Buchwald amination on solid supports: a novel access to a diverse set of 1H-benzotriazoles.
Hartwig-Buchwald amination reactions of bromo- and chloroarenes were performed on solid supports with triazene-linked arenes. Immobilized 2-haloarenes were treated with diverse primary amines and anilines at 100 degrees C under palladium catalysis to yield N-substituted 2-aminoarenes. The latter were alternatively formed through reaction of bromo- and chloroarenes with immobilized primary 2-aminobenzenes. Subsequent acidic cleavage furnished 1H-benzotriazoles in high purities. The two described routes allow a broad range of the substitution pattern of N-substituted 1H-benzotriazoles.
Zimmermann
Viktor
V
Institut für Organische Chemie, Universität Karlsruhe (TH), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
Bräse
Stefan
S
D000143:Acids / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D047028:Macrocyclic Compounds / Q000737:chemistry; D008956:Models, Chemical; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D014226:Triazenes / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis*
D000143:Acids; D000588:Amines; D000814:Aniline Compounds; D047028:Macrocyclic Compounds; D014226:Triazenes; D014230:Triazoles; D010165:Palladium; C012771:benzotriazole; C023650:aniline