2022 Gilead Lecture

From Alkyne Origami to Electron Upconversion: Energy and Stereoelectronics in Reaction Design
Wednesday, 30 March 2022 - 11:30 am
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I will start by discussing the advantages of alkynes as high-energy carbon-rich precursors for extended polyaromatics, stereoelectronics of alkyne cyclizations, the two general patterns of oligoalkyne folding into an aromatic ribbon, and the use of supramolecular effects in the design of traceless directing groups for radical reactions.[1]

In the 2nd part, I will present a mild method for C(sp3)–H amination where basic, radical, and oxidizing species work together in a coordinated sequence of deprotonation, H-atom transfer and electron transfer that forges a new C–N bond.[2]

Finally, I will introduce the phenomenon of electron upconversion, a counterintuitive way to transform weak reductants into strong reductants in a thermodynamically favorable fashion. Such processes enable electrocatalytic transformations where a single electron can drive multiple catalytic cycles. [3]


[1] Alkyne Origami: Folding Oligoalkynes into Polyaromatics. I. V. Alabugin, E. Gonzalez-Rodriguez. Acc. Chem. Res., 2018, 51, 1206.

[2] C. J. Evoniuk, G. d. P. Gomes, S. P. Hill, F. Satoshi, K. Hanson,  I. V. Alabugin, J. Amer. Chem. Soc., 2017, 139, 16210. Q. Elliott, G. Gomes, C. J. Evoniuk, I. V. Alabugin, Chem. Science, 2020, 11, 6539.

[3] Upconversion of Reductants. M. A. Syroeshkin, F. Kuriakose, E. A. Saverina, V. A. Timofeeva, M. P. Egorov, I. V. Alabugin. Angew. Chem. Int. Ed., 2019, 58, 5532.

Speaker Bio

Igor Alabugin grew up in Siberia and earned his PhD from Moscow State University. After a postdoctoral study at the University of Wisconsin-Madison, he joined faculty of the Florida State University (FSU) in 2000. Currently, he is the Cottrell Professor at the FSU Department of Chemistry and Biochemistry where his professional efforts are focused on the discovery of new ways to control chemical structure and reactivity. His interests span development of new chemical transformations, design of light-activated anticancer drugs, and construction of carbon-rich nanostructures. He is also AAAS Fellow, Fulbright Fellow, ACS Cope Scholar Award recipient, and the first recipient of all three FSU Undergraduate Awards: Teaching, Advising, and Research Mentor.