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Synlett 2014; 25(07): 1031-1035
DOI: 10.1055/s-0033-1340956
letter
© Georg Thieme Verlag Stuttgart · New York

1,2-Alkylarylation of Activated Alkenes with Two C–H Bonds by Using Visible-Light Catalysis

Jia-Ling Zhang
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Fax: +(86)73188713642   Email: jhli@hnu.edu.cn   Email: gfjiang@hnu.edu.cn
,
Yu Liu
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Fax: +(86)73188713642   Email: jhli@hnu.edu.cn   Email: gfjiang@hnu.edu.cn
,
Ren-Jie Song
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Fax: +(86)73188713642   Email: jhli@hnu.edu.cn   Email: gfjiang@hnu.edu.cn
,
Guo-Fang Jiang*
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Fax: +(86)73188713642   Email: jhli@hnu.edu.cn   Email: gfjiang@hnu.edu.cn
,
Jin-Heng Li*
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Fax: +(86)73188713642   Email: jhli@hnu.edu.cn   Email: gfjiang@hnu.edu.cn
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Further Information

Publication History

Received: 15 January 2014

Accepted after revision: 17 February 2014

Publication Date:
14 March 2014 (online)

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Abstract

A new visible-light promoted strategy for the difunctionalization of activated alkenes with two C–H bonds has been developed. In the presence of [Ru(bpy)3Cl2], 4-MeOC6H4N2BF4, Na2CO3 and 36 W compact fluorescent light, a variety of N-arylacrylamides underwent the 1,2-alkylarylation reaction with acetonitrile or acetone to give the corresponding functionalized oxindoles in moderate to good yields.

Key words

alkylarylation - alkenes - acetonitrile - acetone - visible-light catalysis - oxindoles

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