General access to aminobenzyl-o-carboranes as a new class of carborane derivatives: entry to enantiopure carborane-amine combinations.
The convenient synthesis of original aminobenzyl-o-carboranes, which represent a new class of nitrogenated carborane derivatives, is described. These novel compounds have been efficiently prepared starting from commercially available aromatic aldehydes and monosubstituted o-carboranes via carboranyl alcohols and chlorides as intermediates. The key step of this methodology is a selective nucleophilic amination under mild conditions that allows the formation of the expected amines while limiting the partial deboronation of the carborane cluster. This general strategy has been applied to the preparation of a wide variety of aminobenzyl-o-carboranes. The extension of this pathway to the synthesis of enantiopure carborane-amine combinations is also described.
Terrasson
Vincent
V
Institut de Ciència de Materials de Barcelona-CSIC, Campus U.A.B. 08193 Bellaterra, Spain.
Planas
José Giner
JG
Prim
Damien
D
Teixidor
Francesc
F
Viñas
Clara
C
Light
Mark E
ME
Hursthouse
Michael B
MB
D000588:Amines / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D000588:Amines; D001896:Boron Compounds; D001554:Benzene