Litcius/Paper detail

Iron-Catalyzed C(sp<sup>3</sup>)–C(sp<sup>3</sup>) Coupling to Construct Quaternary Carbon Centers

Qiao Zhang, Xiangyu Liu, Yandong Zhang, Ming‐Yao Huang, Xinyu Zhang, Shou‐Fei Zhu

2024Journal of the American Chemical Society29 citationsDOI

Abstract

The construction of quaternary carbon centers via C–C coupling protocols remains challenging. The coupling of tertiary C(sp 3 ) with secondary or tertiary C(sp 3 ) counterparts has been hindered by pronounced steric clashes and many side reactions. Herein, we have successfully developed a type of bisphosphine ligand iron complex-catalyzed coupling reactions of tertiary alkyl halides with secondary alkyl zinc reagents and efficiently realized the coupling reaction between tertiary C(sp 3 ) and secondary C(sp 3 ) with high selectivity for the initial instance, which provided an efficient method for the construction of quaternary carbon centers with high steric hindrance. The combination of an iron catalyst and directing group of the substrate makes the great challenging transformation possible.

Topics & Concepts

ChemistrySteric effectsAlkylCatalysisHalideReagentCoupling reactionCarbon fibersLigand (biochemistry)Substrate (aquarium)Medicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryComposite materialBiochemistryGeologyOceanographyReceptorComposite numberMaterials scienceCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsOrganoboron and organosilicon chemistry