Agustin Valles
MIT Department: Chemistry
Faculty Mentor: Prof.Christopher Cummins
Research Supervisor: Chonghe Zhang
Undergraduate Institution: Rice University
Hometown: El Paso, Texas
Biography
Agustin Valles is a rising senior at Rice University studying Chemistry. He is from El Paso, Texas, and the first in his family to attend college in the United States. Agustin is interested in fundamental chemistry research, developing molecular compounds that can facilitate challenging transformations. At Rice University, he has worked in the lab of Dr. Hernandez-Sanchez since January 2023. His project is on the synthesis of metal cluster compounds to investigate how metal-metal interactions can enable the activation of small molecule substrates. As part of the MIT Summer Research Program, Agustin works in the labs of Dr. Christoper Cummins and Dr. Robert Gilliard, exploring the reactivity of diazoborane compounds and their potential as borylene precursors. He plans to pursue a PhD in Inorganic Chemistry and eventually lead his own research program as principal investigator at a research-focused university.
Abstract
Synthesis and Reactivity of Diazoboranes: [3+2] Cycloaddition Chemistry
Agustin Valles1, Chonghe Zhang2, Prof. Christopher C. Cummins2, and
Prof. Robert J. Gilliard2
1Department of Chemistry, Rice University
2 Department of Chemistry, Massachusetts Institute of Technology
Organoboron compounds are valuable intermediates in organic synthesis enabling the
construction of C-C, C-O, C-N, and C-X (where X is a halogen) bonds. They are especially
important in the pharmaceutical industry as they are often required for the synthesis of medicinal compounds such as losartan, the most prescribed pharmaceutical in the world, and abemaciclib, a drug used to treat breast cancer. However, the synthesis of boron containing organic compounds is generally accomplished by transition metal catalysts that are undesirable for large scale synthesis of pharmaceutical compounds. Therefore, there is a need to develop methods for the synthesis of organoboron compounds without employing metal catalysts. In this work we present the synthesis of two N-heterocyclic stabilized diazoborane compounds and explore their reactivity in [3+2] cycloadditions reactions. These reactions proceed at either room temperature or under mild heating to afford novel nitrogen-rich boron heterocycles in a manner that is reminiscent of “click” chemistry of organic azides. Given the utility of diazo compounds in organic synthesis, the diazoboron compound presented herein, represents a major advance towards alternative routes for the synthesis of organoboron compounds.
