The 2-azaallyl anion is one of the earliest known intermediates in synthetic organic chemistry. The past decade has witnessed significant renewed interest in semi-stabilized 2-azaallyl anions as intermediates toward the synthesis of alkaloid natural products and pharmaceutically-relevant scaffolds. Traditionally, generation of 2-azaallyl anions requires deprotonation of the conjugate acid with a strong base under anhydrous and, frequently, anaerobic reaction conditions. Our group, however, has focused on a decarboxylative reaction manifold, typically facilitated by transition metal catalysts, which allows for the generation and alkylation of semi-stabilized 2-azaallyl anions under a broader range of reaction conditions. This talk will recount past successes and recent advances from our group's efforts in this arena. Very recent success involving metal-free cross couplings with 2-azaallyl radicals and aryl halides will also be introduced.
About the speaker :
Jason Chruma earned his PhD from the University of Pennsylvania studying under Prof. Amos B. Smith, III, and this was followed by an NIH post-doctoral fellowship at Columbia University from 2003-2005 with Prof. Ronald C. Breslow. He began his independent career as an Assistant Professor in the Department of Chemistry at the University of Virginia in 2005 before moving in August of 2012 to Sichuan University where he is now a Professor and Director of Doctoral Studies.
Prof. Chruma’s research interest focus on developing new methods for the synthesis of nitrogen-containing organic compounds and other biologically-active natural products involving such “green” methods as transition-metal catalyzed decarboxylative alkylations and intramolecular pericyclic reactions. The intent is to discover new molecular probes and tools to elucidate the biomolecular mechanisms involved in cellular differentiation and aniokis. Additional interests involve the design and synthesis of novel foldamer scaffolds and fluorescent linchpin reagents for bioconjugate synthesis.