Oxygen‐Linked Cyclopentadienyl Rhodium(III) Complexes‐Catalyzed Asymmetric C−H Arylation of Benzo[h]quinolines with 1‐Diazonaphthoquinones
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 issue...
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| Published in | Angewandte Chemie International Edition Vol. 60; no. 28; pp. 15510 - 15516 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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WEINHEIM
Wiley
05.07.2021
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| 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.
A class of chiral cyclopentadienyl ligands (BOCps) bearing an oxygen linker was developed. The BOCpRh complexes are powerful catalysts in an asymmetric C−H arylation of benzo[h]quinolines with 1‐diazonaphthoquinones to construct axially chiral heterobiaryls. Preliminary mechanistic studies suggest that this reaction is likely to proceed via an electrophilic C−H rhodation and subsequent coupling with 1‐diazonaphthoquinones. |
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| AbstractList | 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. 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. A class of chiral cyclopentadienyl ligands (BOCps) bearing an oxygen linker was developed. The BOCpRh complexes are powerful catalysts in an asymmetric C−H arylation of benzo[h]quinolines with 1‐diazonaphthoquinones to construct axially chiral heterobiaryls. Preliminary mechanistic studies suggest that this reaction is likely to proceed via an electrophilic C−H rhodation and subsequent coupling with 1‐diazonaphthoquinones. 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. |
| Author | Gu, Qing Pan, Chongqing Yin, Si‐Yong Wang, Shao‐Bo You, Shu‐Li |
| Author_xml | – sequence: 1 givenname: Chongqing surname: Pan fullname: Pan, Chongqing organization: Center for Excellence in Molecular Synthesis – sequence: 2 givenname: Si‐Yong surname: Yin fullname: Yin, Si‐Yong organization: Center for Excellence in Molecular Synthesis – sequence: 3 givenname: Shao‐Bo surname: Wang fullname: Wang, Shao‐Bo organization: Center for Excellence in Molecular Synthesis – sequence: 4 givenname: Qing surname: Gu fullname: Gu, Qing organization: Center for Excellence in Molecular Synthesis – sequence: 5 givenname: Shu‐Li orcidid: 0000-0003-4586-8359 surname: You fullname: You, Shu‐Li email: slyou@sioc.ac.cn organization: Center for Excellence in Molecular Synthesis |
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| Keywords | heterobiaryl ACTIVATION ENANTIOSELECTIVE SYNTHESIS CHIRAL (CPRH)-RH-X ALKYLATION BIARYL COMPOUNDS axial chirality FUNCTIONALIZATION OLEFINATION LIGANDS CONSTRUCTION chiral cyclopentadienyl BOND rhodium |
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| Notes | Dedicated to Professor Christian Bruneau for his contributions to catalysis |
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| Snippet | Chiral cyclopentadienyl rhodium (CpRh) complex‐catalyzed asymmetric C−H functionalization reactions have witnessed a significant progress in organic synthesis.... Chiral cyclopentadienyl rhodium (CpRh) complex-catalyzed asymmetric C-H functionalization reactions have witnessed a significant progress in organic synthesis.... |
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| SubjectTerms | axial chirality Chemistry Chemistry, Multidisciplinary chiral cyclopentadienyl heterobiaryl Physical Sciences rhodium Science & Technology |
| Title | Oxygen‐Linked Cyclopentadienyl Rhodium(III) Complexes‐Catalyzed Asymmetric C−H Arylation of Benzo[h]quinolines with 1‐Diazonaphthoquinones |
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