Design and Generation of Boryl Radicals for Direct Deoxygenation of Alcohols via C–O Homolysis

The hydroxy group (–OH) is well represented in organic chemistry and is present in 37% of commercial therapeutics, 69% of natural products and numerous biomasses. Despite their ubiquitous nature, the development of methods to directly transform hydroxy groups in a mild and less wasteful way has been seriously neglected. This, therefore, pushes for a method to interface organoboron chemistry with photoredox catalysis to achieve the direct activation of hydroxy groups for its functionalization with boryl radicals. Our lab has recently developed a new boronic ester that could potentially undergo photochemical oxidation. We anticipate that this Xpin-protected boronate (Bxpin) has the potential to generate a boryl radical via photoredox catalysis for alcohol abstraction to generate an alkyl radical. This alkyl radical could then undergo a wide variety of radical addition processes such as the Giese-type reaction, the Minisci reaction, acylation, and metallaphotoredox cross-coupling. The unique reactivity in this proposed project will help illuminate our fundamental understanding of photochemical C–O bond cleavage and boryl radical formation.

Faculty Supervisor:

Dennis Hall

Student:

Partner:

Westfälische Wilhelms-Universität Münster

Discipline:

Physics

Sector:

Pharmaceuticals; Sustainability & the Environment

University:

University of Alberta

Program: