Palladium(II)‐Catalyzed Selective Arylation of Tertiary C−H Bonds of Cyclobutylmethyl Ketones Using Transient Directing Groups
Jin‐Tang Cheng, Li‐Jun Xiao, Shaoqun Qian, Zhe Zhuang, An Liu, Jin‐Quan Yu
Abstract
-catalyzed tertiary C-H activation of cyclobutylmethyl ketones using a transient directing group. An electron-deficient 2-pyridone ligand was identified as the optimal external ligand to enable tertiary C-H activation. A variety of cyclobutylmethyl ketones bearing quaternary carbon centers was readily accessed without preinstalling internal directing groups in up to 81 % yield and >95 : 5 regioisomeric ratios of tertiary C-H arylation to β-methylene (β-methyl) or γ-C-H arylation.
Topics & Concepts
PalladiumCatalysisChemistryTransient (computer programming)Medicinal chemistryOrganic chemistryComputer scienceOperating systemCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSynthesis and Catalytic Reactions