Nickel-Catalyzed Reductive Csp<sup>3</sup>–Ge Coupling of Alkyl Bromides with Chlorogermanes
Peng Guo, Xiaobo Pang, Ke Wang, Pei‐Feng Su, Qiu‐Quan Pan, Guanyu Han, Qian Shen, Zhenzhen Zhao, Wen‐Hua Zhang, Xing‐Zhong Shu
Abstract
Reductive cross-coupling provides facile access to organogermanes, but it remains largely unexplored. Herein we report a nickel-catalyzed reductive Csp3–Ge coupling of alkyl bromides with chlorogermanes. This work has established a new method for producing alkylgermanes. The reaction proceeds under very mild conditions and tolerates various functionalities including ether, alcohol, alkene, nitrile, amine, ester, phosphonates, amides, ketone, and aldehyde. The application of this method to the modification of bioactive molecules is demonstrated.
Topics & Concepts
ChemistryNitrileReductive eliminationCatalysisAlkylNickelAldehydeAlkeneAlcoholAmine gas treatingEtherKetoneCombinatorial chemistryReductive aminationMoleculeOrganic chemistryCoupling (piping)Coupling reactionMedicinal chemistryMechanical engineeringEngineeringCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAdvanced Synthetic Organic Chemistry