College of Science
70 Convergent access to asymmetric [2.2]paracyclophane and derivatives via Ni-catalyzed cross electrophile cyclization and deamination contraction
Alison Nopper; Andrew Roberts; Myles Lovasz; and Christopher Frederick
Faculty Mentor: Andrew Roberts (Chemistry, University of Utah)
Cyclophane structures are a fascinating class of molecules that are found in a widerange of natural products, pharmaceuticals, and chemical compounds, including important ligands like Phanephos. These structures are highly valued in chemistry for their unique properties and potential applications, particularly in drug development and materials science. However, despite their significance, cyclophanes can be challenging to synthesize. Traditional methods for creating these molecules often involve complex and labor-intensive processes, such as modifying an existing cyclophane or constructing intricate chemical rings that are reshaped later in the synthesis. These approaches can limit the variety of cyclophanes that can be produced, especially when trying to introduce multiple substitutions or heteroatoms like nitrogen or oxygen into the structure.
To overcome these challenges, the Roberts Group at the University of Utah’s Department of Chemistry has developed an innovative strategy known as the build-cyclize-contract logic. This approach begins with simple molecules called tertiary amines, which are relatively easy to make and manipulate. The Roberts Group’s method involves building these starting molecules into more complex structures, then cyclizing (or forming rings) and finally contracting the structure to form dense, multi-ringed molecules. This new strategy opens up new possibilities for synthesizing a broader range of complex cyclophane compounds, including those with substitutions or heteroatoms, which are difficult to achieve with traditional methods. Our group’s work has the potential to significantly expand the toolkit available for synthetic chemists, enabling the design of more diverse and functional molecules for a variety of applications.
Bibliography
ACS Omega, 2020, 5(35):22314–22324
Beilstein J Org Chem, 2015; 11: 1274–1331
LibreText, 2021
Master Org. Chem, 2023
Nat Commun 7, 2016, 11052
Progress in Polymer Science, 2008, 33:346-364