907209-82-9

Upstream product

• 3282-30-2 pivaloyl chloride 
• 106-47-8 4-chloro-aniline 
• 74-88-4 methyl iodide 
• 65854-91-3 N-(4-chlorophenyl)-2,2-dimethylpropionamide 
• 932-96-7 N-methyl(p-chloroaniline) 

Downstream Products

• 907209-99-8 [N-(4-chlorophenyl)pivalamido]methyl acetate 

Relevant academic research and scientific papers

Palladium-catalyzed oxidation of Boc-protected N-methylamines with IOAc as the oxidant: A Boc-directed sp3 C-H bond activation

Pd-catalyzed selective oxidation of Boc-protected N-methylamines with IOAc as the oxidant is described. Evidence for the involvement of a Boc-directed C-H activation process is provided.

Meta Selective C-H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction

An electrostatically directed meta borylation of sterically biased and unbiased substrates is described. The borylation follows an electrostatic interaction between the partially positive and negative charges between the ligand and substrate. With this strategy, it has been demonstrated that a wide number of challenging substrates, especially 4-substituted substrates, can selectively be borylated at the meta position. Moreover, unsubstituted substrates also displayed excellent meta selectivity. The reaction employs a bench-stable ligand and proceeds at a milder temperature, precluding the need to synthesize a bulky and sophisticated ligand/template.

Pd(II)-Catalyzed Chemoselective Acetoxylation of C(sp2)-H and C(sp3)-H Bonds in Tertiary Amides

Palladium-catalyzed chemoselective C(sp2)-H and C(sp3)-H acetoxylation of synthetically useful tertiary amides is reported under relatively mild reaction conditions. This protocol proceeds through the assistance of a weakly coordinated directing group (Ca? O) and requires low catalyst (1.0 mol %) loading. Diverse functionalities, such as C(sp2)-Cl, C(sp3)-Cl,-CF3,-COOEt, and-NO2 groups, including morpholinyl, piperazinyl, and pyrrolidinyl heterocycles, are compatible under the reaction conditions. Further functionalization of this protocol is demonstrated by hydrolysis to alcohols, alcohol-acids, as well as reduction to tertiary amines. A preliminary kinetic isotope effect study supported the rate-limiting C-H bond activation process.

α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp3)-H Coupling

Pd(II)-catalyzed α-C(sp3)-H arylation of pyrrolidines, piperidines, azepanes, and N-methylamines with arylboronic acids has been developed for the first time. This transformation is applicable to wide arrays of pyrrolidines and boronic acids, including heteroaromatic boronic acids. A diastereoselective one-pot heterodiarylation of pyrrolidines has also been achieved.