Oxidative C–H Homodimerization of Phenylacetamides

Abstract

A range of secondary and tertiary phenylacetamides undergo oxidative homodimerization to afford biaryls. The reaction proceeds under palladium catalysis in the presence of a copper cocatalyst and oxygen and is most effective for electron-rich substrates.

Amide Formation Using In Situ Activation of Carboxylic Acids with [Et2NSF2]BF4

“…provided the crude product, which was isolated by flash chromatography (ethyl acetate/hexane, 50:50) to give the desired product (196 mg, 96 %) as a white solid. Spectral data of 2 were identical with those previously reported 20,21…”

Mechanistic details of the cobalt-mediated dehydrogenative dimerization of aminoquinoline-directed benzamides

“…[5][6][7][8][9] Many advances in this area of research have relied on the use of expensive secondrow transition metal (e.g., palladium, rhodium, and ruthenium) complexes and thus limits their application in large-scale industrial processes. [10][11][12] Therefore, catalysts that incorporate relatively inexpensive and earth-abundant rst-row transition metals are attractive alternatives. Recent research by several groups has led to the discovery of multiple cobalt and copper promoted aryl-aryl and aryl-heteroaryl dimerization reactions.…”

Directed Iron-Catalyzedortho-Alkylation and Arylation: Toward the Stereoselective Catalytic Synthesis of 1,2-Disubstituted Planar-Chiral Ferrocene Derivatives

“…The dehydrogenative dimerization of ODG-substituted arenes, e.g., under cobalt promotion or cobalt, palladium , or ruthenium catalysis, is well-known but unprecedented in ferrocene chemistry. Jäckle et al succeeded in the stereoselective Negishi coupling and dimerization of a chiral ferrocenyl sulfoxide .…”