CuI-catalyzed amination of arylhalides with guanidines or amidines: a facile synthesis of 1-H-2-substituted benzimidazoles.
CuI/L5 (N,N'-dimethylethylenediamine) proves to be an efficient catalyst system for the amination of arylhalides with guanidines. The same catalyst system is then successfully applied to the one-step synthesis of 1-H-2-amino-benzimidazoles through tandem aminations of 1,2-dihaloarenes in modest yields. This methodology is also applicable for the preparation of 1-H or 1-substutituted 2-aryl- or 2-alkyl-benzimidazoles.
Deng
Xiaohu
X
Johnson & Johnson Pharmaceutical Research & Development, LLC 3210 Merryfield Row, San Diego, California 92121, USA. xdeng@its.jnj.com
McAllister
Heather
H
Mani
Neelakandha S
NS
D000578:Amidines / Q000737:chemistry*; D000586:Amination; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005029:Ethylenediamines / Q000737:chemistry; D019791:Guanidine / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000578:Amidines; D001562:Benzimidazoles; D005029:Ethylenediamines; D006846:Hydrocarbons, Halogenated; D007454:Iodides; C027450:dimethylethylenediamine; D003300:Copper; C073870:cuprous iodide; D019791:Guanidine