Journal article
Copper-Catalyzed Three-Component Carboazidation of Alkenes with Acetonitrile and Sodium Azide.
- Bunescu A Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
- Ha TM Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
- Wang Q Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
- Zhu J Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
- 2017-06-27
Published in:
- Angewandte Chemie (International ed. in English). - 2017
English
A copper-catalyzed three-component reaction of alkenes, acetonitrile, and sodium azide afforded γ-azido alkyl nitriles by formation of one C(sp3 )-C(sp3 ) bond and one C(sp3 )-N bond. The transformation allows concomitant introduction of two highly versatile groups (CN and N3 ) across the double bond. A sequence involving the copper-mediated generation of a cyanomethyl radical and its subsequent addition to an alkene, and a C(sp3 )-N bond formation accounted for the reaction outcome. The resulting γ-azido alkyl nitrile can be easily converted into 1,4-diamines, γ-amino nitriles, γ-azido esters, and γ-lactams of significant synthetic value.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1002/anie.201705353
- PMID 28651036
- Persistent URL
- https://sonar.ch/global/documents/231229
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