Synthesis of Aryl and Heteroaryl Diazophosphonates via Palladium-Catalyzed Cross-Coupling and Their Application in Rhodium-Catalyzed Cyclopropanation

High Resolution Image Download MS PowerPoint Slide Aryl and heteroaryl diazophosphonates are valuable intermediates in organic synthesis and medicinal chemistry. This study presents an efficient and versatile strategy for their synthesis via palladium-catalyzed cross-coupling reactions using readily available diazophosphonate precursors and diverse aryl- and heteroaryl iodides. The method demonstrates excellent yields, broad functional group tolerance, and scalability. Notably, the synthetic utility of the resulting diazophosphonates is showcased through a rhodium-catalyzed cyclopropanation, yielding complex cyclopropane derivatives with high diastereo- and enantioselectivity. Highly enantioselective cyclopropanation was also feasible. This combined palladium- and rhodium-catalyzed approach offers a robust, scalable, and stereoselective pathway for accessing multifunctional scaffolds, thereby expanding the capabilities of modern synthetic chemistry.