34259-60-4Relevant academic research and scientific papers
Copper-Catalyzed Intermolecular Functionalization of Unactivated C(sp3)-H Bonds and Aliphatic Carboxylic Acids
Mao, Runze,Bera, Srikrishna,Turla, Aurélya Christelle,Hu, Xile
supporting information, p. 14667 - 14675 (2021/09/18)
Intermolecular functionalization of C(sp3)-H bonds and aliphatic carboxylic acids enables the efficient synthesis of high value-added organic compounds from readily available starting materials. Although methods involving hydrogen atom transfer have been developed for such functionalization, these methods either work for only activated C(sp3)-H bonds or bring in a narrow set of functional groups. Here we describe a Cu-catalyzed process for the diverse functionalization of both unactivated C(sp3)-H bonds and aliphatic carboxylic acids. The process is enabled by the trapping of alkyl radicals generated through hydrogen atom abstraction by arylsulfonyl-based SOMO-philes, which introduces a large array of C, N, S, Se, and halide-based functional groups. The chemoselectivity can be switched from C-H functionalization to decarboxylative functionalization by matching the bond dissociation energy of the hydrogen atom transfer reagent with that of the target C-H or O-H bond.
Sulfur-Assisted Ring Expansion of the Potassium Salts of 1-Vinylcyclobutanols. A Versatile Synthesis of Cyclohexanones
Cohen, Theodore,Yu, Lin-Chen,Daniewski, Wlodzimierz M.
, p. 4596 - 4600 (2007/10/02)
Readily available 2-(phenylthio)-1-vinylcyclobutanols undergo a facile potassium hydride induced ring expansion to 4-(phenylthio)cyclohexanones.The sulfur substituent plays a key role.Evidence for a fragmentation to an enone-anion intermediate is discusse
