Synthesis and reactions
of organobismuth compounds
First disclosed all the way back in 1857, organobismuth compounds, or compounds containing a C - Bi bond, are broadly related to more familiar Grignard, organozinc and organolithium reagents with some notable differences. In contrast to the aforementioned reagents, aryl bismuth compounds are robust to air and moisture. Additionally, despite its identity as a heavy metal, compounds of bismuth and the metal itself are far less toxic than the more familiar mercury or lead, so much so that we regularly use it in medicines!
Bismuth organometallics have access to multiple oxidations states with diverse reactivity, from transition-metal like behavior and cross-coupling to the Wild West of radical chemisty.
Our goals with this area are threefold:
(1) develop new ways to efficiently access organobismuth compounds
(2) develop new reactions with bismuth chemistry to broaden the chemical toolbox
(3) at all stages, lower the barrier to entry for the bismuth-curious
Silicon-directed functionalization of organic molecules
Silanes are an integral piece of many aspects of our lives, from coatings, to tubing, shampoos, cosmetics, sterile packaging and filters. Given the high volume demand of these chemicals, we (humanity) have developed incredibly efficient routes to form carbon-silicon bonds, rivaling the prowess of enzymes.
In the Chiappini lab, we are deeply interested in taking these abundant silicon feedstocks and using the element’s unique reactivity to enable new disconnections in organic chemistry.
At the moment our interests are honed on carbon-nitrogen bond formation directed by silicon, but we hope to expand to looking at a wide array of new bond formations.
Synthesizing the osmolytes that make our ocean tick
The microorganisms that live in the top layers of our oceans, estuaries and rivers are an integral piece of Earth’s biosphere, making the majority of our oxygen! But the life of a planktonic organism isn’t easy! They constantly need to fight against predation and the threat of losing water to their environment, much in the way our fingers shrivel up after a long pool day.
To prevent this, these organisms synthesize an array of small molecules, called osmolytes, which help abrogate this threat. These organic molecules are among the most abundant in our oceans and we have an incredibly limited understanding of what they do beyond regulation osmotic pressure. In collaboration with Dr. Winn Johnson’s group at UNCW we are synthesizing standards of these osmolytes with the goal of pursuing isotopic tracing to better understand how the plankton use these fascinating little molecules.