Recent advances in electrochemical deoxygenation reactions of organic compounds

Abstract

As naturally abundant and recyclable industrial feedstock, alcohols and carboxylic acids have drawn tremendous attention in medicinal chemistry and polymer chemistry. The selective C-O cleavage of hydroxyl group represents appealing...

A convergent paired electrochemical strategy for decarboxylative C(sp2)–C(sp3) bond formation

“…8 In that approach, an unmodified alkyl alcohol underwent conversion to an alkyl bromide through an Appel reaction with anodic generated PPh 3 ·Br 2 , subsequently paired with Ni-catalyzed cathodic reductive cross-coupling to achieve formal dehydroxylative C(sp 2 )–C(sp 3 ) bond formation. Building on this foundation, the current study explores the potential of anodically generated PPh 3 ·Br 2 to activate carboxylic acids, 9,10 yielding acyloxytriphenylphosphonium ions. In the presence of NHPI, these ions are envisioned to be subsequently transformed into NHPI esters.…”

Photoredox‐Catalyzed Generation of Tertiary Anions from Primary Amines via a Radical Polar Crossover

“…[3] Given their importance and ease of access, amines are an attractive synthetic handle for the development of new deaminative methodologies to diversify a molecular scaffold. [4] Despite the ubiquity of amines, deaminative cross-coupling reactions are surprisingly limited compared tocross-coupling technologies employing carboxylic acids, [5] alcohols, [6] and organohalides. [7] This can be attributed in part to the poor leaving group abilities of amines as well as their inherent basicity.…”