Ruthenium-Catalyzed Intermolecular [2 + 2] Cycloaddition of Unactivated Allenes and Alkynes with Unusual Regioselectivity
Chaoshen Zhang, Herman H. Y. Sung, Ian D. Williams, Yun‐Dong Wu, Jianwei Sun
Abstract
High Resolution Image Download MS PowerPoint Slide Described here is an efficient protocol for intermolecular [2 + 2] cycloaddition of unactivated and unsymmetrical allenes and alkynes with unusual regioselectivity, counterintuitively favoring the most hindered isomer. CpRu(MeCN) 3 PF 6 served as a uniquely effective catalyst, providing diverse 3-alkylidenecyclobutenes with a broad scope and good functional group compatibility. Both experiments and DFT studies provided important insights into the mechanism, particularly the unusual regioselectivity.
Topics & Concepts
ChemistryCycloadditionRegioselectivityIntermolecular forceFunctional groupScope (computer science)StereochemistryComputational chemistryIntramolecular forceDensity functional theoryCombinatorial chemistryGroup (periodic table)AlleneMedicinal chemistryCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis