Electrochemical B−H Nitrogenation: Access to Amino Acid and BODIPY‐Labeled <i>nido</i>‐Carboranes
Long Yang, Becky Bongsuiru Jei, Alexej Scheremetjew, Rositha Kuniyil, Lutz Ackermann
Abstract
Abstract Electrocatalyzed oxidative B−H nitrogenations of nido ‐carborane ( nido ‐7,8‐C 2 B 9 H 12 − ) with N‐heterocycles have been established, enabling the preparation of various N‐substituted nido ‐carboranes without chemical oxidants or metal catalyst under ambient conditions. The electrolysis manifold occurred with high levels of efficiency as well as chemo‐ and position‐ selectivity, employing sustainable electricity as the sole oxidant. The strategy set the stage for a user‐friendly access to novel amino acid and fluorogenic boron‐dipyrrin (BODIPY)‐labeled nido ‐carborane hybrids.
Topics & Concepts
BODIPYChemistryCarboraneBoronElectrochemistryBrønsted–Lowry acid–base theorySelectivityMedicinal chemistryCatalysisStereochemistryCombinatorial chemistryOrganic chemistryFluorescenceElectrodePhysicsPhysical chemistryQuantum mechanicsBoron Compounds in ChemistryRadiopharmaceutical Chemistry and ApplicationsPharmacological Effects and Toxicity Studies