Direct Arylation of C(sp2)–H Bonds in Anilines

The direct arylation of allylic sp3 C–H bonds via organocatalysis and photoredox catalysis

Gold-catalyzed direct arylation.

Biaryls (two directly connected aromatic rings, Ar(1)-Ar(2)) are common motifs in pharmaceuticals, agrochemicals, and organic materials. Current methods for establishing the Ar(1)-Ar(2) bond are dominated by the cross-coupling of aryl halides (Ar(1)-X) with aryl metallics (Ar(2)-M). We report that, in the presence of 1 to 2 mole percent of a gold catalyst and a mild oxidant, a wide range of are...

Allocolchicinoid synthesis via direct arylation.

[reaction: see text] A formal enantioselective synthesis of allocolchicine and a synthesis of a C-ring analogue have been achieved by employing an intramolecular direct arylation of an aryl chloride to form the biaryl carbon-carbon bond and the seven-membered ring.

Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds.

Many directing group containing arenes can now be arylated or alkylated under palladium, rhodium, or ruthenium catalysis.1 Even arenes lacking traditional directing groups can be functionalized representing the most atom-efficient method for creation of arylaryl bonds.2 However, in this case, regioselectivity issues often are unsolved. An exception can be found in recent elegant work by Fagnou ...

CoPc-catalyzed selective radical arylation of anilines with arylhydrazines for synthesis of 2-aminobiaryls.

CoPc-catalyzed selective radical arylation of anilines with arylhydrazines to afford 2-aminobiaryls in moderate to good yields is described.