Knowledge Bank

In the synthesis of increasingly complex molecules, many different tools are being employed to create difficult to access bonds. Transition-metal catalysis is one of the more widely studied and used methods, but there are drawbacks such as cost and toxicity that have called for greener alternatives. Investigations into the use of a relatively unstudied class of compounds called nitrimines has revealed potential for their employment in generating moieties with limited accessibility. Because of the previous success of using nitrimines to create carbon-nitrogen bonds, they are being investigated as a new family of reagents in the sustainable construction of carbon-carbon and carbon-fluorine bonds. The success of the carbon-carbon coupling reactions using nitrimines can be seen in the broad scope of the reaction as well as the E/Z selectivity control and application to the synthesis of a small target molecule. In addition, recent findings have shown promise with nitrimine use in creating vinyl fluorides and trifluoromethyl groups.