2,4-Disubstituted pyrroles are a common substructure in biologically active compounds.1 Therefore, their synthesis, especially through the use of inexpensive materials, is essential. Copper (I) salts have been reported to catalyze the cyclization of aryloxy-enynes with amines to yield substituted pyrroles.2 We hypothesized that this strategy could be applied to the cyclization of β-alkynyl enamines, the major product of an iron-catalyzed carboamination process recently discovered in our lab.3 5 equivalents of CuCl was found to cyclize β-alkynyl enamines to pyrroles in good yields. Carboamination and cyclization can be performed in a two-step, one-pot protocol, avoiding difficult initial separation of the enamine from iron-containing side products.
Grace Murphy was born and raised in St. Louis, MO. At Saint Louis University, she studies chemistry and is an undergraduate researcher in the Neely Lab. In the fall, Grace will attend the University of Minnesota for graduate school where she plans on studying Organometallic Chemistry. When she has free time outside of the lab and class, Grace enjoys running, baking, and painting.
Dr. Neely has been an amazing teacher and mentor. Through having the opportunity to do research in her lab I have not only improved my synthesis skills but realized the Organometallic Chemistry and Catalysis are passions of mine. Where I am as a scientist is credited to her kindness and knowledge. I cannot thank her enough for all she has done and can only hope to be half as good of a scientist that she is one day.
I don't even know how to describe Corey and the extent that he has helped me that will give him justice. Corey is my graduate student who I have been lucky enough to work on this project with. He has taught me everything I know in the lab and been patient with me throughout the process. If I ever have any problem, Corey has a solution. This project would be nowhere without his hard work and intelligence.