UC San Diego

Carbenes have a long history of being classed as highly reactive species, whose isolation was deemed impossible. However, a paradigm shift occurred over two decades ago when the first stable carbene was reported. Since then, the field of stable carbene chemistry has flourished and applications in numerous fields of chemistry have been found. One unlikely application comes from their ability to act as stabilizing entities. Indeed, a wide variety of previously unattainable transition metal and main group species have been isolated via carbene stabilization. In this manuscript, carbenes will be utilized to isolate highly reactive species based on Group 13 and 15 elements. The first part of this manuscript will describe the design and synthesis of boron centered nucleophiles supported by carbenes. Then, it will be shown that the steric environment of the carbene plays a pivotal role in protecting a highly reactive fragment. The electronic properties of carbenes are also a crucial characteristic to consider and we demonstrate that with the appropriate carbene framework, a single element can be stabilized in several oxidation states. Finally, we will demonstrate that a phosphorus analogue of a carbene, which has eluded isolation so far, can be stabilized with the appropriate framework.