First application of an efficient and versatile ligand for copper-catalyzed cross-coupling reactions of vinyl halides with N-heterocycles and phenols.
2-Pyridin-2-yl-1H-benzoimidazole L3 is presented as a new, efficient, and versatile bidentate N-donor ligand suitable for the copper-catalyzed formation of vinyl C-N and C-O bonds. This inexpensive and easily prepared ligand facilitates copper-catalyzed cross-coupling reactions of alkenyl bromides and iodides with N-heterocycles and phenols to afford the desired cross-coupled products in good to excellent yields with full retention of stereochemistry. This method is particularly noteworthy given its efficiency, that is, mild reaction conditions, low catalyst loading, simplicity, versatility, and exceptional level of functional group tolerance.
Kabir
M Shahjahan
MS
Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, USA.
Lorenz
Michael
M
Namjoshi
Ojas A
OA
Cook
James M
JM
D001562:Benzimidazoles / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
C547267:2-pyridin-2-yl-1H-benzoimidazole; D001562:Benzimidazoles; D003432:Cross-Linking Reagents; D006571:Heterocyclic Compounds; D006846:Hydrocarbons, Halogenated; D008024:Ligands; D010636:Phenols; D011725:Pyridines; D014753:Vinyl Compounds; D003300:Copper