Event



Organic Chemistry Seminar: Dr. Keary Engle

"Alkenes as Universal Functional Group Progenitors"
Apr 4, 2022 at - | Chemistry Complex
Carol Lynch Lecture Hall
inquiries please contact
Rosa M. Vargas
rvargas@sas.upenn.edu
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keary

Dr. Keary Engle 

Scripps Research 

 

"Alkenes as Universal Functional Group Progenitors"

 

-Alkenes are inexpensive, widely available chemical feedstocks that can be sourced from petroleum or renewable resources. The goal of research in the Engle lab is to develop novel alkene difunctionalization reactions, thereby introducing two new functional groups at each of the alkenyl carbon atoms. The products formed from these transformations conveniently map onto molecules that are of academic and industrial importance, including many widely used pharmaceutical agents. Our central hypothesis is that coordination of a π-Lewis acidic metal, such as palladium(II), to the alkene will promote attack of a nucleophile and that the resultant organometallic species can be trapped with an electrophile to furnish the desired 1,2-difunctionalized product. This latter operation involves a high-oxidation-state intermediate, from which selective reductive elimination can be achieved. In the overall net transformation, one of the two new functional groups is introduced in the form of a nucleophile, and the other in the form of an electrophile. Lewis basic groups on the substrate are used to coordinate to the metal catalysts, controlling the site-selectivity and suppressing side reactions. These concepts have been used to invent a series of useful reactions, such as three-component alkene carboamination, where an amino group and an aryl/alkyl/alkenyl group are selectively added across an alkene.

 

https://englelab.com

HOST: Kozlowski