Thesis Defense: “Decarbonylative Cross-Electrophile Coupling Methods to Form C-C Bonds”

Carboxylic acids represent one of the most commercially abundant feedstocks, and identifying transformations to utilize these substrates represents a growing area of interest. Most often, decarbonylative methods to furnish C–C bonds can be limited by the reversibility of CO loss from the system, as well as, in transition-metal catalyzed systems, the potential formation of highly toxic, volatile, flammable metal carbonyls. This talk focuses on my work into the development of decarbonylative cross-electrophile coupling methods to form C–C bonds of aryl esters with a variety of alkyl sources. In the first half, mechanistic insight and setup design were crucial for understanding and capitalizing on a fast, reversible oxidative addition and decarbonylation sequence to furnish C(sp2)–C(sp3) bonds. The second half of my talk expands upon this by utilizing Metal-Organic Frameworks (MOFs) as bench-stable CO capture reagents to promote decarbonylation at lower temperatures in non-amide solvents using an organic reductant.