26278-74-0Relevant articles and documents
Employing a robustness screen: Rapid assessment of rhodium(III)-catalysed C-H activation reactions This paper is dedicated to Professor Paul A. Wender, a great scientist, teacher and mentor
Collins, Karl D.,Glorius, Frank
, p. 7817 - 7825 (2013)
Following the discovery of new synthetic methodology, an assessment of its potential utility in real synthetic problems is highly desirable to facilitate its application. Herein, we describe an assessment of two contemporary rhodium catalysed C-H activati
Rhodium(III)-Catalyzed C-H Activation: Ligand-Controlled Regioselective Synthesis of 4-Methyl-Substituted Dihydroisoquinolones
Barber, Joyann S.,Scales, Stephanie,Tran-Dubé, Michelle,Wang, Fen,Sach, Neal W.,Bernier, Louise,Collins, Michael R.,Zhu, Jinjiang,McAlpine, Indrawan J.,Patman, Ryan L.
, p. 5689 - 5693 (2019)
Rh-catalyzed C-H functionalization of O-pivaloyl benzhydroxamic acids with propene gas provides access to 4-methyl-substituted dihydroisoquinolones. Good to excellent levels of regioselectivity are achieved using [CptRhCl2]2 as a precatalyst under optimized conditions. Thorough examination of aryl/heteroaryl O-pivaloyl hydroxamic acid substrates, ligand effects on C-H site selectivity, alkene scope, and demonstration of scale are discussed within.
RhIII-Catalyzed C?H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones
Shaaban, Saad,Davies, Caitlin,Merten, Christian,Flegel, Jana,Otte, Felix,Strohmann, Carsten,Waldmann, Herbert
, p. 10729 - 10734 (2020/07/25)
RhIII-catalyzed C?H functionalization reaction yielding isoindolinones from aryl hydroxamates and ortho-substituted styrenes is reported. The reaction proceeds smoothly under mild conditions at room temperature, and tolerates a range of functional groups. Experimental and computational investigations support that the high regioselectivity observed for these substrates results from the presence of an ortho-substituent embedded in the styrene. The resulting isoindolinones are valuable building blocks for the synthesis of bioactive compounds. They provide easy access to the natural-product-like compounds, isoindolobenzazepines, in a one-pot two-step reaction. Selected isoindolinones inhibited Hedgehog (Hh)-dependent differentiation of multipotent murine mesenchymal progenitor stem cells into osteoblasts.
Divergent Synthesis of Tunable Cyclopentadienyl Ligands and Their Application in Rh-Catalyzed Enantioselective Synthesis of Isoindolinone
Cui, Wen-Jun,Wu, Zhi-Jie,Gu, Qing,You, Shu-Li
supporting information, p. 7379 - 7385 (2020/08/19)
A series of rhodium complexes bearing sterically and electronically tunable cyclopentadienyl ligands, prepared by utilizing Co2(CO)8-mediated [2+2+1] cyclization as a key step, were synthesized. In the presence of 2.5 mol% of CpmRh4, unprecedented enantioselective [4+1] annulation reaction of benzamides and alkenes was achieved with a broad substrate scope under mild reaction conditions, providing a variety of isoindolinones with excellent regio-and enantioselectivity (up to 94% yield, 97:3 er). Preliminary mechanistic studies suggest that the reaction involves an oxidative Heck reaction and an intramolecular enantioselective alkene hydroamination reaction.
