Undergraduate Research & Scholarships

Hamile Khan Rose Hills

Functional Group Tolerant Methylation of Arylboronic Esters

The proposed project tackles a significant challenge in organic synthesis, specifically the development of a functional group tolerant method for the methylation of arylboronic esters. The main focus of this project entails the transformation of an aryl boronic ester into an aryl-methyl group via a copper-catalyzed methylation reaction with the slow release of methyl iodide. Previous methods were unable to tolerate functional groups due to the presence of stoichiometric base, resulting in the methylation of nucleophilic functional groups present on the aryl boronic ester substrate. In order to overcome this challenge, a new approach is suggested for the methylation of arylboronic esters that simultaneously generates and consumes the methylating reagent and base in situ. This method would enable a formal C–H methylation when combined with C–H borylation of inactivated arenes. This method would be a useful tool for medicinal chemists because of the great demand for effective methods to selectively incorporate methyl groups into complex scaffolds for drug development. Methyl groups play a crucial role in the field, and this new method will enable researchers to introduce them in a more efficient and selective manner. Previous methods for the methylation of arylboronic esters have been limited in scope, and a new method is needed that can be applied to a broad range of substrates. 

Message To Sponsor

I am deeply grateful for the funding I have received and would like to express my gratitude. Your generosity has enabled me to take advantage of a unique opportunity to expand my research experience and skills at UC Berkeley during the summer. I am excited to work alongside renowned faculty members and experienced researchers, and I am confident that this opportunity will equip me with the knowledge and tools needed to make significant contributions to my field of study.
Major: B.S. Chemistry
Mentor: Jenna Manske
Sponsor: SURF Rose Hills
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