Novel N-Heterocyclic Carbene Ligands for Transition-Metal Catalysis

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Invention Summary:

N-heterocyclic carbenes (NHCs) are tremendously valuable ligands in homogeneous catalysis. Some of the most popular ligands are NHCs that have demonstrated success in a number of organometallic transformations of great interest both in academia and industry. However, synthesizing NHCs poses challenges due to their air and moisture sensitivity, necessitating rigorous conditions and specialized equipment. 

Rutgers researchers have developed a family of NHCs that offer a wide range of steric hindrance, electronic tunability by introducing novel modifications to the NHC scaffold such as: a non-classical triazole backbone, amino-decorated L-shaped bidentate ligand, iPr# (1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene). Furthermore, a direct and facile synthesis method of the novel Pd(II)-NHC pre-catalysts has been developed from readily available anilines as throw- away ligands. The availability of various aniline scaffolds, including those with structural and electronic diversity, offers advantages in the design and fine-tuning of challenging cross-coupling reactions. This wide variety of ligand structures provides a range of steric and electronic factors to tune for key reactions in organometallic catalysis. 

Market Applications:

• Pharmaceutical synthesis, fine chemical production, functional materials and polymers synthesis 
• Development of catalysts for various synthetically valuable reactions 
• Offers a family of NHC ligands with novel structural changes to the backbone

Advantages:

• Can provide robust chemical stability under varying conditions 

• Some can be used to produce commercial salts and in cross-coupling reactions used by many fields 

• Simple synthesis from inexpensive and readily available materials 

• Potential for facile diversification and reactivity tuning through steric and electronic effects 

Publications:

Intellectual Property & Development Status: Provisional application filed. Patent pending. Available for licensing and/or research collaboration. For any business development and other collaborative partnerships, contact:  marketingbd@research.rutgers.edu