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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 45, 2015 - Issue 10
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Original Articles

Copper-Catalyzed Cyanopropylation of Activated Alkenes

Shi TangCollege of Chemistry and Chemical Engineering, Central South University, Changsha, China;College of Chemistry and Chemical Engineering, Jishou University, Jishou, ChinaCorrespondence[email protected]
,
Zhi-Hao LiCollege of Chemistry and Chemical Engineering, Jishou University, Jishou, China
,
Dong ZhouCollege of Chemistry and Chemical Engineering, Jishou University, Jishou, China
,
You-Lin DengCollege of Chemistry and Chemical Engineering, Jishou University, Jishou, China
,
Guo-Liang DingCollege of Chemistry and Chemical Engineering, Jishou University, Jishou, China
,
Qian ZhangCollege of Chemistry and Chemical Engineering, Jishou University, Jishou, China
,
Li-Ya LiuCollege of Chemistry and Chemical Engineering, Jishou University, Jishou, China
&
Shu-Hua LiCollege of Chemistry and Chemical Engineering, Central South University, Changsha, China
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Pages 1231-1239 | Received 08 Dec 2014, Published online: 19 Mar 2015
 
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Abstract

A practical copper-catalyzed alkylarylation of activated alkenes with azobisisobutyronitrile (AIBN) and beyond has been developed, in which incorporation of 3o 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 3o nitrile moiety.

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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.

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