TfOH-catalyzed regioselective -alkylation of indazoles with diazo compounds
Selective alkylation of indazoles is still a highly challenging topic in chemistry and the synthesis of important molecules. Herein, a novel highly selective N 2 -alkylation of indazoles with diazo compounds is described in the presence of TfOH. Unlike the traditional metal- and base-catalysed versi...
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| Published in | Chemical communications (Cambridge, England) Vol. 58; no. 44; pp. 6429 - 6432 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Published |
30.05.2022
|
| Online Access | Get full text |
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| Abstract | Selective alkylation of indazoles is still a highly challenging topic in chemistry and the synthesis of important molecules. Herein, a novel highly selective
N
2
-alkylation of indazoles with diazo compounds is described in the presence of TfOH. Unlike the traditional metal- and base-catalysed version, this protocol highlights the regioselectivity of alkylation of indazoles and a metal-free catalysis system, affording
N
2
-alkylated products in good to excellent yields with high regioselectivity (
N
2
/
N
1
up to 100/0) and excellent functional group tolerance. Furthermore, a gram scale synthesis was conducted successfully to give rise to the corresponding products. Mechanistic studies through control experiments provide plausible mechanistic proposals.
A novel highly selective
N
2
-alkylation of indazoles with diazo compounds is described in good to excellent yields with high regioselectivity (
N
2
/
N
1
up to 100/0) and excellent functional group tolerance. |
|---|---|
| AbstractList | Selective alkylation of indazoles is still a highly challenging topic in chemistry and the synthesis of important molecules. Herein, a novel highly selective
N
2
-alkylation of indazoles with diazo compounds is described in the presence of TfOH. Unlike the traditional metal- and base-catalysed version, this protocol highlights the regioselectivity of alkylation of indazoles and a metal-free catalysis system, affording
N
2
-alkylated products in good to excellent yields with high regioselectivity (
N
2
/
N
1
up to 100/0) and excellent functional group tolerance. Furthermore, a gram scale synthesis was conducted successfully to give rise to the corresponding products. Mechanistic studies through control experiments provide plausible mechanistic proposals.
A novel highly selective
N
2
-alkylation of indazoles with diazo compounds is described in good to excellent yields with high regioselectivity (
N
2
/
N
1
up to 100/0) and excellent functional group tolerance. |
| Author | Jin, Jingru Chen, Fener Yan, Jingyu Wang, Wei Yan, Zhewei Yan, Qiongjiao Jiang, Haipeng He, Hangli Wang, Haifeng |
| AuthorAffiliation | Department of Chemistry Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs Pharmaceutical Research Institute Fudan University Engineering Center of Catalysis and Synthesis for Chiral Molecules Wuhan Institute of Technology School of Chemical Engineering & Pharmacy |
| AuthorAffiliation_xml | – name: Fudan University – name: Department of Chemistry – name: Pharmaceutical Research Institute – name: Wuhan Institute of Technology – name: Engineering Center of Catalysis and Synthesis for Chiral Molecules – name: School of Chemical Engineering & Pharmacy – name: Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs |
| Author_xml | – sequence: 1 givenname: Hangli surname: He fullname: He, Hangli – sequence: 2 givenname: Jingyu surname: Yan fullname: Yan, Jingyu – sequence: 3 givenname: Jingru surname: Jin fullname: Jin, Jingru – sequence: 4 givenname: Zhewei surname: Yan fullname: Yan, Zhewei – sequence: 5 givenname: Qiongjiao surname: Yan fullname: Yan, Qiongjiao – sequence: 6 givenname: Wei surname: Wang fullname: Wang, Wei – sequence: 7 givenname: Haipeng surname: Jiang fullname: Jiang, Haipeng – sequence: 8 givenname: Haifeng surname: Wang fullname: Wang, Haifeng – sequence: 9 givenname: Fener surname: Chen fullname: Chen, Fener |
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| DOI | 10.1039/d2cc01404a |
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| Notes | Electronic supplementary information (ESI) available. CCDC For ESI and crystallographic data in CIF or other electronic format see DOI https://doi.org/10.1039/d2cc01404a 2144543 |
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| Snippet | Selective alkylation of indazoles is still a highly challenging topic in chemistry and the synthesis of important molecules. Herein, a novel highly selective
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| Title | TfOH-catalyzed regioselective -alkylation of indazoles with diazo compounds |
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