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Rhodium-Catalyzed Asymmetric Cyclopropanation of Indoles with N-Triftosylhydrazones.
Angew Chem Int Ed Engl
December 2024
Department of Chemistry, Northeast Normal University, Changchun, 130024, China.
Herein we report a general rhodium-catalyzed asymmetric intermolecular dearomative cyclopropanation of indoles using trifluoromethyl N-triftosylhydrazones as carbene precursors. The reaction enables the rapid construction of diverse cyclopropane-fused indolines bearing a trifluoromethylated quaternary stereocenter with high enantioselectivity (up to 99 % ee). This mild method exhibits broad substrate scope, tolerating various functional groups, and can even be utilized for the late-stage diversification of complex bioactive molecules.
View Article and Find Full Text PDFCobalt- or rhodium-catalyzed synthesis of 1,2-dihydrophosphete oxides C-H activation and formal phosphoryl migration.
Chem Sci
April 2024
School of Chemistry and Chemical Engineering, Shaanxi Normal University (SNNU) Xi'an 710062 P. R. China
A highly stereo- and chemoselective intermolecular coupling of diverse heterocycles with dialkynylphosphine oxides has been realized cobalt/rhodium-catalyzed C-H bond activation. This protocol provides an efficient synthetic entry to functionalized 1,2-dihydrophosphete oxides in excellent yields the merger of C-H bond activation and formal 1,2-migration of the phosphoryl group. Compared with traditional methods of synthesis of 1,2-dihydrophosphetes that predominantly relied on stoichiometric metal reagents, this catalytic system features high efficiency, a relatively short reaction time, atom-economy, and operational simplicity.
View Article and Find Full Text PDFSystematic Studies of Functional Group Tolerance and Chemoselectivity in Carbene-Mediated Intramolecular Cyclopropanation and Intermolecular C-H Functionalization.
Chem Pharm Bull (Tokyo)
March 2024
Graduate School of Pharmaceutical Sciences, Chiba University.
Generating reliable data on functional group compatibility and chemoselectivity is essential for evaluating the practicality of chemical reactions and predicting retrosynthetic routes. In this context, we performed systematic studies using a functional group evaluation kit including 26 kinds of additives to assess the functional group tolerance of carbene-mediated reactions. Our findings revealed that some intermolecular heteroatom-hydrogen insertion reactions proceed faster than intramolecular cyclopropanation reactions.
View Article and Find Full Text PDFTuning Selectivity and Stability in Heteroleptic Lanthanide Adducts by Ligand Design.
Inorg Chem
February 2024
Department of Inorganic and Analytical Chemistry, University of Geneva, 30 quai E. Ansermet, CH-1211 Geneva 4, Switzerland.
Terdentate ligands - and their heteroleptic [Ln(hfac)] complexes (Ln = La, Eu, Gd, Er, or Y; H-hfac = 1,1,1,5,5,5-hexafluoropentane-2,4-dione) exhibit multifactorial correlations between the ligand's structural frameworks, including their level of preorganization and steric congestion and their affinities and selectivities for catching the trivalent lanthanide containers [Ln(hfac)]. The polyaromatic ligand scaffolds could be stepwise modulated via lanthanide-template synthetic strategies, using intermolecular rhodium-catalyzed insertion reactions. The increasing level of preorganization along the → → series leads to a duality in which larger thermodynamic formation constants with lanthanides in CDCl are accompanied by an unexpected decrease in the Ln-N affinities in the solid state, which could be assigned to a limited match between the lanthanide size and the enlarged preorganized cavities.
View Article and Find Full Text PDFTransition-Metal-Catalyzed C-C Bond Formation from C-C Activation.
Acc Chem Res
November 2023
Department of Chemistry, Fudan University, Shanghai 200433, P. R. China.
ConspectusC-C single bonds are ubiquitous in organic compounds. The activation and subsequent functionalization of C-C single bonds provide a unique opportunity to synthesize conventionally inaccessible molecules through the rearrangement of carbon skeletons, often with a favorable atom and step economy. However, the C-C bonds are thermodynamically and kinetically inert.
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