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Activation of Carbon-Carbon Single Bonds

Project Full Title:

Development of New Organic Reactions Using Transition Metal-Catalysis

Project Mentor(s):

Johnson,Jeffrey

Project Mentor(s) EMail:

jjohnson@hope.edu

Project Start Date:

5/13/2019

Project End Date:

7/19/2019

Project Description:

An opportunity is available to contribute to an ongoing research program at Hope College in the general areas of transition metal-catalyzed carbon-carbon single bond activation and the development of new organic reactions. In addition to basic research and experimental techniques common to organic and inorganic chemistry, students working on projects in these areas can expect to gain experience in the reactivity and manipulation of air sensitive compounds, the analysis and understanding of reaction mechanisms, and the process of developing new organic reactions.

Within the realm of traditional organic chemistry, very few reactions involve the cleavage of a carbon-carbon sigma bond. These kinetically and thermodynamically stable bonds are inert under a vast majority of reaction conditions. The use of transition metals, however, provides the means for activation of these bonds. Recently developed rhodium-based catalysts are capable of breaking carbon-carbon bonds adjacent to ketones, ultimately allowing substitution of one side of the ketone. Current methodology is limited to a relatively small number of substrates containing limited functionality, as the reaction requires high temperatures and long reaction times.

Despite current limitations, there is great potential in the activation of carbon-carbon bonds. The development of mild and selective reaction conditions could provide means for the synthesis of complex molecules through routes impossible using traditional organic methodology. In addition, highly active cleavage catalysts promise a means of generating basic chemical building blocks from readily available biological feedstocks.

Work in the Johnson group at Hope College will focus upon a number of aspects of the carbon-carbon bond activation. These will include 1) further understanding of the reaction mechanism, 2) the use of mechanistic information for the rational development of more active catalysts for the extension of substrate scope, and 3) the development of new organic transformations involving the cleavage and further reaction of carbon-carbon single bonds.

Summer research details Students can expect 10 40-hour weeks--during this time, attendance at department events, including seminars, research lunches, research poster day, and professional development events, is mandatory. Students are also expected to attend and contribute to regular group meetings. There are also plenty of group social events planned throughout the summer!

While the dates listed are for summer research, work continues throughout the academic year. Hope students are encouraged to explore research possibilities during the spring semester. While experiences are available in many capacities, primary options include research for credit, no credit, or as part of a CHEM 256 independent project.

For additional information, see: hope.edu/directory/people/johnson-jeffrey/index.html. Also feel free to contact Prof. Jeff Johnson at jjohnson@hope.edu.

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