Copper-Catalyzed Three-Component Carboazidation of Alkenes with Acetonitrile and Sodium Azide

A copper-catalyzed three-component reaction of alkenes, acetonitrile, and sodium azide afforded gamma-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 coppermediated 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 g-azido alkyl nitrile can be easily converted into 1,4-diamines, g-amino nitriles, g-azido esters, and g-lactams of significant synthetic value.


Published in:
Angewandte Chemie International Edition, 56, 35, 10555-10558
Year:
2017
Publisher:
Weinheim, Wiley-Blackwell
ISSN:
1433-7851
Keywords:
Laboratories:




 Record created 2017-08-22, last modified 2018-01-28


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