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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Copper-Catalyzed Three-Component Carboazidation of Alkenes with Acetonitrile and Sodium Azide
Ala Bunescu1, Tu M Ha1, Qian Wang1
1Laboratory 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.
Abstract:
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.
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