Copper-Catalyzed Cyanopropylation of Activated Alkenes

Abstract

A practical copper-catalyzed alkylarylation of activated alkenes with azobisisobutyronitrile (AIBN) and beyond has been developed, in which incorporation of 3^o nitrile moiety into an oxindole scaffold proceeded smoothly through cascade radical addition/C(sp²)-H cyclization. The use of readily available AIBN as radical source and inexpensive CuI as catalyst, as well as broad substrate scope and the simplicity of operation and handling, make this protocol a highly attractive approach to oxindoles bearing 3^o nitrile moiety.

GRAPHICAL ABSTRACT

Keywords:

• 3° nitrile
• AIBN
• Cu catalysis
• cyanopropylation
• oxindole

SUPPORTING INFORMATION

Full experimental details, ¹H and ¹³C NMR spectra, and x-ray data for product 3a for this article can be accessed on the publisher’s website.