Department of Chemistry & Biochemistry Seminar, Dr. Sebastien Laulhe

Department of Chemistry & Biochemistry Seminar

Friday, September 11th, 2020

1:30pm – 2:45pm

Zoom ID: 960 452 0800

Password: Activation

N-Chloroimides as Novel Multifaceted Amination Reagents: Enabling C–H Aminations and Deoxyaminations

Speaker: Dr. Sébastien Laulhé, Indiana University Purdue University

Abstract: The formation of C–N bonds is of crucial importance to the pharmaceutical, agrochemical, and material science industries. Traditionally, these C–N bonds have been synthesized via SN2 substitutions, reductive amination, or other metal-catalyzed transformations. Deoxyamination of alcohols and carboxylic acids, such as the Mitsunobu reaction or peptide coupling reactions, are also used to generate alkyl amines and amides, but these reactions require the use of highly toxic and explosive activating reagents. Herein, we propose to use N-chloroimides to perform efficient and atom-economical amination reactions via both radical C–H activation and deoxyamination strategies. In detail, we have developed various methodologies that afford alkyl amines and amides using N-chloroimides both as our activating agent and as our nitrogen source. Such transformations are more atom-economical and safer than current strategies since the reagents used are significantly less toxic and are fully incorporated in the final products.

Biography: Seb grew up in Venezuela, Mexico, and France. While pursuing a Master’s Degree in chemical engineering from the National Engineering Graduate School of Chemistry (ENSCM) in Montpellier, France, he started a Ph.D. program at the University of Louisville with Michael H. Nantz in 2008. Together, they expanded the role of the oximation reaction by developing new aminooxy containing reagents for applications in synthesis and quantitative high throughput GC-MS analysis. After graduating in 2013, Seb became a postdoctoral associate at Duke University working with Jennifer L. Roizen. There, he developed new Suzuki- Miyaura cross-coupling methodologies for the selective functionalization of ortho-halopyridines. In August 2016, Seb started his independent career at IUPUI as an assistant professor in the Department of Chemistry and Chemical Biology.