19480-12-7Relevant academic research and scientific papers
Copper catalyzed C(sp3)-H bond alkylation via photoinduced ligand-to-metal charge transfer
Treacy, Sean M.,Rovis, Tomislav
supporting information, p. 2729 - 2735 (2021/03/01)
Utilizing catalytic CuCl2 we report the functionalization of numerous feedstock chemicals via the coupling of unactivated C(sp3)-H bonds with electron-deficient olefins. The active cuprate catalyst undergoes Ligand-to-Metal Charge Transfer (LMCT) to enable the generation of a chlorine radical which acts as a powerful hydrogen atom transfer reagent capable of abstracting strong electron-rich C(sp3)-H bonds. Of note is that the chlorocuprate catalyst is an exceedingly mild oxidant (0.5 V vs SCE) and that a proposed protodemetalation mechanism offers a broad scope of electron-deficient olefins, offering high diastereoselectivity in the case of endocyclic alkenes. The coupling of chlorine radical generation with Cu reduction through LMCT enables the generation of a highly active HAT reagent in an operationally simple and atom economical protocol.
Iron-Catalyzed C(sp 3)-H Alkylation through Ligand-to-Metal Charge Transfer
Kang, Yi Cheng,Rovis, Tomislav,Treacy, Sean M.
supporting information, p. 1767 - 1771 (2021/08/20)
We report the FeCl 3-catalyzed alkylation of nonactivated C(sp 3)-H bonds. Photoinduced ligand-to-metal charge transfer at the iron center generates chlorine radicals that then preferentially abstract hydrogen atoms from electron-ric
Efficient Synthesis of Polysubstituted 1,5-Benzodiazepinone Dipeptide Mimetics via an Ugi-4CR-Ullmann Condensation Sequence
Ballet, Steven,Elsocht, Mathias,Hollanders, Charlie,Van Den Hauwe, Robin
supporting information, p. 1719 - 1724 (2021/08/20)
An efficient three-step synthesis towards 3-amino-1,4-benzodiazepin-2-one derivatives is presented. The versatile Ugi-4-component reaction (Ugi-4CR) and Boc deprotection is followed by a ligand-free Ullmann condensation. This protocol allows the rapid construction of a diverse array of substituted 1,5-benzodiazepinones. Since Ugi-based products are typically limited by their 'inert' C -terminal amides, the use of a convertible ('cleavable') isocyanide was envisaged and resulted in building blocks that can be made SPPS compatible. To demonstrate the potential of this novel synthetic route, the design and preparation of novel phenylurea-1,5-benzodiazepin-4(5 H)-one dipeptide mimetics with potential CCK2-antagonist properties is reported.
