Transition‐Metal‐Free Alkylation of N‐Heterocycles with Nitriles via Heteroarylphosphonium Intermediates
Abstract: Heteroarylphosphonium salts are easily accessible, versatile intermediates in functionalization of N‐heterocycles. Direct C−C bond formation by net substitution of the phosphine has so far required transition metal catalysts, the use of strongly basic reagents or redox catalysis. Here we describe a C−C bond formation in direct reactions of benzothiazol‐2‐yl‐phosphonium and pyridin‐4‐yl‐phosphonium salts and nitrile anions which, together with the direct synthesis of phosphonium salts from benzothiazoles and pyridines, constitutes an efficient and simple two‐step protocol for C−H functionalization of these heterocycles under mild conditions.
- Location
-
Deutsche Nationalbibliothek Frankfurt am Main
- Extent
-
Online-Ressource
- Language
-
Englisch
- Bibliographic citation
-
Transition‐Metal‐Free Alkylation of N‐Heterocycles with Nitriles via Heteroarylphosphonium Intermediates ; day:22 ; month:02 ; year:2024 ; extent:6
European journal of organic chemistry ; (22.02.2024) (gesamt 6)
- Creator
- DOI
-
10.1002/ejoc.202301233
- URN
-
urn:nbn:de:101:1-2024022314153723005278
- Rights
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
-
14.08.2025, 10:47 AM CEST
Data provider
This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Schömberg, Fritz
- Perić, Milica
- Vilotijević, Ivan
Other Objects (12)
Transition‐Metal‐Free Alkylation of N‐Heterocycles with Nitriles via Heteroarylphosphonium Intermediates
Synthesis of divergent N-heterocycles enabled by nitrene or gold carbene intermediates
Alpha-aminonitriles as key intermediates in the synthesis of natural products and N-heterocycles
Aziridines Cross-Dimerize to Larger N-Heterocycles
Stereoselectively fluorinated N-heterocycles: a brief survey
Cu(OTf) 2 ‐Mediated Cross‐Coupling of Nitriles and N‐Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products **
Cu(OTf) 2 ‐Mediated Cross‐Coupling of Nitriles and N‐Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products **
Electrochemical access to biologically potent five-membered N-heterocycles
Photodehydrogenation of N-Heterocycles with Hexagonal Boron Carbon Nitride
Polyfunctionalizations of N-heterocycles via chemo- and regioselective metalations
Iron(II)‐Catalyzed Aerobic Biomimetic Oxidation of N‐Heterocycles
A sustainable thermochemical conversion of animal biomass to N-heterocycles
Transition‐Metal‐Free Alkylation of N‐Heterocycles with Nitriles via Heteroarylphosphonium Intermediates
Synthesis of divergent N-heterocycles enabled by nitrene or gold carbene intermediates
Alpha-aminonitriles as key intermediates in the synthesis of natural products and N-heterocycles
Aziridines Cross-Dimerize to Larger N-Heterocycles
Stereoselectively fluorinated N-heterocycles: a brief survey
Cu(OTf) 2 ‐Mediated Cross‐Coupling of Nitriles and N‐Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products **
Cu(OTf) 2 ‐Mediated Cross‐Coupling of Nitriles and N‐Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products **
Electrochemical access to biologically potent five-membered N-heterocycles
Photodehydrogenation of N-Heterocycles with Hexagonal Boron Carbon Nitride
Polyfunctionalizations of N-heterocycles via chemo- and regioselective metalations
Iron(II)‐Catalyzed Aerobic Biomimetic Oxidation of N‐Heterocycles
A sustainable thermochemical conversion of animal biomass to N-heterocycles
Transition‐Metal‐Free Alkylation of N‐Heterocycles with Nitriles via Heteroarylphosphonium Intermediates
Synthesis of divergent N-heterocycles enabled by nitrene or gold carbene intermediates
Alpha-aminonitriles as key intermediates in the synthesis of natural products and N-heterocycles
Aziridines Cross-Dimerize to Larger N-Heterocycles
Stereoselectively fluorinated N-heterocycles: a brief survey
Cu(OTf) 2 ‐Mediated Cross‐Coupling of Nitriles and N‐Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products **
Cu(OTf) 2 ‐Mediated Cross‐Coupling of Nitriles and N‐Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products **
Electrochemical access to biologically potent five-membered N-heterocycles
Photodehydrogenation of N-Heterocycles with Hexagonal Boron Carbon Nitride
Polyfunctionalizations of N-heterocycles via chemo- and regioselective metalations
Iron(II)‐Catalyzed Aerobic Biomimetic Oxidation of N‐Heterocycles