Regioselective aerobic oxidative Heck reactions with electronically unbiased alkenes: efficient access to α-alkyl vinylarenes.

Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative Heck reactions.

Pd-catalyzed aerobic oxidative coupling of vinylboronic acids and electronically unbiased alkyl olefins provides regioselective access to 1,3-disubstituted conjugated dienes. Catalyst-controlled regioselectivity is achieved by using 2,9-dimethylphenanthroline as a ligand. The observed regioselectivity is opposite to that observed from a traditional (nonoxidative) Heck reaction between a vinyl b...

Regioselective palladium-catalyzed olefination of coumarins via aerobic oxidative Heck reactions.

Pd-catalyzed oxidative Heck reactions of coumarins were developed via simultaneous C-H functionalization at the C3 position of coumarins under aerobic conditions.

Nickel-catalyzed Mizoroki-Heck reaction of aryl sulfonates and chlorides with electronically unbiased terminal olefins: high selectivity for branched products.

Achieving high selectivity in the Heck reaction of electronically unbiased alkenes has been a longstanding challenge. Using a nickel-catalyzed cationic Heck reaction, we were able to achieve excellent selectivity for branched products (≥19:1 in all cases) over a wide range of aryl electrophiles and aliphatic olefins. A bidentate ligand with a suitable bite angle and steric profile was key to ob...

Aerobic oxidative Heck/dehydrogenation reactions of cyclohexenones: efficient access to meta-substituted phenols.

Oxidative Arylation

The addition of aryl groups to unactivated olefins represents a direct approach to C!C bond construction. Pd-catalyzed coupling of aryl halides with alkenes, the Heck reaction, offers a viable approach to arylation. However, terminal unactivated olefins often display low reactivity in Heck reactions and can yield mixtures of styrenes and allyl arenes owing to poor regiocontrol in the b-hydride ...