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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Synthesis of Aryl and Heteroaryl Diazophosphonates via Palladium-Catalyzed Cross-Coupling and Their Application in
Yasir Naeem1, Duc Ly1, Huw M L Davies1
1Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
Abstract:
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.
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