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Oxygen‐Linked Cyclopentadienyl Rhodium(III) Complexes‐Catalyzed Asymmetric C−H Arylation of Benzo[ h ]quinolines with 1‐Diazonaphthoquinones
- Source :
- Angewandte Chemie International Edition. 60:15510-15516
- Publication Year :
- 2021
- Publisher :
- Wiley, 2021.
-
Abstract
- Chiral cyclopentadienyl rhodium (CpRh) complex-catalyzed asymmetric C-H functionalization reactions have witnessed a significant progress in organic synthesis. In sharp contrast, the reported chiral Cp ligands are limited to C-linked Cp and are often synthetically challenging. To address these issues, we have developed a novel class of tunable chiral cyclopentadienyl ligands bearing oxygen linkers, which were efficient catalysts for C-H arylation of benzo[h]quinolines with 1-diazonaphthoquinones, affording axially chiral heterobiaryls in excellent yields and enantioselectivity (up to 99 % yield, 98.5:1.5 er). Mechanistic studies suggest that the reaction is likely to proceed by electrophilic C-H activation, and followed by coupling of the cyclometalated rhodium(III) complex with 1-diazonaphthoquinones.
- Subjects :
- 010405 organic chemistry
chemistry.chemical_element
General Medicine
General Chemistry
010402 general chemistry
01 natural sciences
Medicinal chemistry
Oxygen
Catalysis
0104 chemical sciences
Rhodium
chemistry.chemical_compound
Cyclopentadienyl complex
chemistry
Axial chirality
Yield (chemistry)
Electrophile
Organic synthesis
Subjects
Details
- ISSN :
- 15213773 and 14337851
- Volume :
- 60
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie International Edition
- Accession number :
- edsair.doi.dedup.....ac76f345252e750bb072378bfead4c59