Computational Studies of Iridium (III)-Catalyzed Tandem C-H Activation
Location
Science Center: Bent Corridor
Document Type
Poster - Open Access
Start Date
4-28-2023 12:00 PM
End Date
4-28-2023 2:00 PM
Abstract
Carbon-hydrogen bonds are ubiquitous in organic compounds but are typically inert. However, advancement in organometallic reactions has enabled chemists to transform these bonds and release the energy stored inside them. Such C-H activation reactions are highly attractive for developing more environmentally friendly syntheses. Our research is concerned with the study of two successive C-H activations of both C(sp2)-H and C(sp3)-H bonds of an anisole reactant aided by an iridium-III catalyst bound to a Cp* ligand. Using density functional theory (DFT) calculations, we aimed to optimize transition states for this reaction and determine its energetics. Our work has yielded unexpected results, identifying an intermediate transition state resulting from oxidative addition to the transition metal catalyst with a stabilized metal hydride intermediate, not the expected concerted metalation deprotonation (CMD) process. These findings can be used to help guide future study and understanding of these reactions.
Keywords:
Computational chemistry, C-H activation, Organic chemistry, Catalysis
Recommended Citation
Ih, Marisa and Chen, Shuming, "Computational Studies of Iridium (III)-Catalyzed Tandem C-H Activation" (2023). Research Symposium. 7.
https://digitalcommons.oberlin.edu/researchsymp/2023/posters/7
Major
Biochemistry; Clarinet Performance
Project Mentor(s)
Shuming Chen, Chemistry and Biochemistry
2023
Computational Studies of Iridium (III)-Catalyzed Tandem C-H Activation
Science Center: Bent Corridor
Carbon-hydrogen bonds are ubiquitous in organic compounds but are typically inert. However, advancement in organometallic reactions has enabled chemists to transform these bonds and release the energy stored inside them. Such C-H activation reactions are highly attractive for developing more environmentally friendly syntheses. Our research is concerned with the study of two successive C-H activations of both C(sp2)-H and C(sp3)-H bonds of an anisole reactant aided by an iridium-III catalyst bound to a Cp* ligand. Using density functional theory (DFT) calculations, we aimed to optimize transition states for this reaction and determine its energetics. Our work has yielded unexpected results, identifying an intermediate transition state resulting from oxidative addition to the transition metal catalyst with a stabilized metal hydride intermediate, not the expected concerted metalation deprotonation (CMD) process. These findings can be used to help guide future study and understanding of these reactions.
