1613614-49-5

Upstream product

• 100-39-0 benzyl bromide 
• 57145-06-9 α,α-diethyldihydrocinnamic acid methyl ester 
• 5343-57-7 2-ethyl-2-benzyl-butyric acid 
• 578-66-5 8-amino quinoline 
• 816-11-5 2-ethyl-butyric acid methyl ester 
• 1328064-88-5 2,2-dimethyl-3-phenyl-N-(quinolin-8-yl)propanamide 
• 75-24-1 trimethylaluminum 

Downstream Products

• 1613614-64-4 C₂₂H₂₂N₂O 

Relevant academic research and scientific papers

Iron-Catalyzed Directed C(sp2)-H and C(sp3)-H Functionalization with Trimethylaluminum

Conversion of a C(sp2)-H or C(sp3)-H bond to the corresponding C-Me bond can be achieved by using AlMe3 or its air-stable diamine complex in the presence of catalytic amounts of an inorganic iron(III) salt and a diphosphine along with 2,3-dichlorobutane as a stoichiometric oxidant. The reaction is applicable to a variety of amide substrates bearing a picolinoyl or 8-aminoquinolyl directing group, enabling methylation of a variety of (hetero)aryl, alkenyl, and alkyl amides. The use of the mild aluminum reagent prevents undesired reduction of iron and allows the reaction to proceed with catalyst turnover numbers as high as 6500.

Copper-catalyzed site-selective intramolecular amidation of unactivated C(sp3)-H bonds

The intramolecular dehydrogenative amidation of aliphatic amides, directed by a bidentate ligand, was developed using a copper-catalyzed sp3 C-H bond functionalization process. The reaction favors predominantly the C-H bonds of β-methyl groups over the unactivated methylene C-H bonds. Moreover, a preference for activating sp3 C-H bonds of β-methyl groups, via a five-membered ring intermediate, over the aromatic sp2 C-H bonds was also observed in the cyclometalation step. Additionally, sp3 C-H bonds of unactivated secondary sp3 C-H bonds could be functionalized by favoring the ring carbon atoms over the linear carbon atoms. Getting ahead on tams: The intramolecular dehydrogenative amidation of aliphatic amides, directed by a bidentate ligand, was developed using a copper-catalyzed sp 3 C-H bond functionalization process to deliver β-lactams. The reaction favors the C-H bonds of β-methyl groups over the unactivated methylene C-H bonds, as well as aromatic C(sp2)-H bonds and unactivated secondary C(sp3)-H bonds of rings.