Kirill Lukin

A General Method for the Synthesis of Unsymmetrically Substituted Ureas via Palladium-Catalyzed Amidation

A general and practical method for the preparation of unsymmetrically substituted ureas has been developed utilizing palladium-catalyzed amidation. Both aryl bromides and chlorides, as well as heteroaryl chlorides, have been coupled to aryl, benzyl, and aliphatic ureas by using a novel nonproprietary bipyrazole ligand (bippyphos).

Synthesis of a TRPV1 receptor antagonist.

A five-step synthesis of a TRPV1 receptor antagonist 1 is described. The key step involves a novel palladium-catalyzed amidation reaction of 4-chloro-1-methylindazole 8 with the benzyl urea 9 to form the unsymmetrically substituted urea 1.

Practical Method for Asymmetric Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds Utilizing an In Situ Prepared Rhodium Catalyst

A new practical method for the asymmetric Michael addition of arylboronic acids to alpha,beta-unsaturated carbonyl compounds utilizing in situ generated chiral rhodium-binap-based catalyst has been developed to address the unavailability of the preformed catalysts. While maintaining high levels of enantioselectivity reported for the preformed catalysts, the new method provides a convenient access to either enantiomeric form of the product and allows for a substantial reductions in both the boronic acid and the catalyst loads.