Metal-free Cyclization of Alkenes Toward Perfluorinated Oxindoles

doi:10.11944/j.issn.1000-0518.2015.11.150108

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (11): 1246-1252.DOI: 10.11944/j.issn.1000-0518.2015.11.150108

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Metal-free Cyclization of Alkenes Toward Perfluorinated Oxindoles

TANG Shi^a^b^*(),LI Zhihao^a,DENG Youlin^a,GAN Yabing^a,YUAN Shiliang^a,ZHOU Xiangqi^a

^aCollege of Chemistry and Chemical Engineering,Jishou University,Jishou,Hu'nan 427000,China
^bCollege of Chemistry and Chemical Engineering,Central South University,Changsha 410083,China

Received:2015-03-23 Accepted:2015-06-25 Published:2015-11-02 Online:2015-11-02
Contact: TANG Shi
Supported by:
Supported by the National Natural Science Foundation of China(No.21462017), Opening Fund of Key Laboratory of Hu'nan Forest Product and Chemical Industry Engineering(No.JDZ201402)

Abstract

Abstract:

A metal-free cyclization reaction of activated alkenes with nonafluorobutyl iodide toward perfluorinated oxindoles was developed. In the presence of azodiisobutyronitrile(AIBN), various N-arylacrylamide underwent radical cyclization smoothly to afford a series of synthetically important perfluorinated oxindoles in 53%~85% yields. This work provides a novel high efficient, cheap and green route for the synthesis of perfluorinated oxindoles having potential medicinal values.

Key words: metal-free, azodiisobutyronitrile, C—H cyclization, radical, perfluorinated oxindole

TANG Shi, LI Zhihao, DENG Youlin, GAN Yabing, YUAN Shiliang, ZHOU Xiangqi. Metal-free Cyclization of Alkenes Toward Perfluorinated Oxindoles[J]. Chinese Journal of Applied Chemistry, 2015, 32(11): 1246-1252.

References

[1]	Prakash G S,Chacko S. Novel Nucleophilic and Electrophilic Fluoroalkylation Methods[J]. Curr Opin Drug Discov Develop,2008,11(6):793-802.
[2]	Trost B,Brennan M K. Asymmetric Syntheses of Oxindole and Indole Spirocyclic Alkaloid Natural Products[J]. Synthesis,2009,2009(18):3003-3025.
[3]	Marti C,Carreira E M,Construction of Spiro[pyrrolidine-3,3'-oxindoles]-Recent Applications to the Synthesis of Oxindole Alkaloids[J]. Eur J Org Chem,2003,2003(12):2209-2219.
[4]	MAI Wenpeng,WANG Jitao,YANG Liangru,et al.Progress in Synthesis of Oxindoles by Radical Addition-Cyclization[J]. Chinese J Org Chem,2014,34(10):1958-1965(in Chinese). 买文鹏,王继涛,杨亮茹,等. 自由基加成/关环反应合成1,3-二氢吲哚-2-酮的研究进展[J]. 有机化学,2014,34(10):1958-1965.
[5]	Li L,Den M,Zheng S,et al.Metal-Free Direct Intramolecular Carbotrifluoromethylation of Alkenes to Functionalized Trifluoromethyl Azaheterocycles[J]. Org Lett,2014,16(2):504-507.
[6]	Mu X,Wu T,Wang H,et al.Palladium-Catalyzed Oxidative Aryltrifluoromethylation of Activated Alkenes at Room Temperature[J]. J Am Chem Soc,2012,134(2):878-881.
[7]	Yang F,Klumphu P,Liang Y,et al.Copper-catalyzed Trifluoromethylation of N-Arylacrylamides “on water” at Room Temperature[J]. Chem Commun,2014,50(8):936-938.
[8]	Zhang L,Li Z,Liu Z. A Free-Radical Cascade Trifluoromethylation/Cyclization of N-Arylmethacrylamides and Enynes with Sodium Trifluoromethanesulfinate and Iodine Pentoxide[J]. Org Lett,2014,16(14):3688-3691.
[9]	Wei W,Wen J,Yang D,et al.Metal-Free Direct Trifluoromethylation of Activated Alkenes with Langlois' Reagent Leading to CF3-Containing Oxindoles[J]. J Org Chem,2014,79(9):4225-4230.
[10]	Liang S,Yang X, Wang Y,et al.Metal-Free Trifluoromethylation and Arylation of Alkenes:Domino Synthesis of Oxindole Derivatives[J]. Adv Synth Catal,2014,356(5):1021-1028.
[11]	Tang X J,Thomoson C S,Dolbier W R. Photoredox-Catalyzed Tandem Radical Cyclization of N-Arylacrylamides: General Methods To Construct Fluorinated 3,3-Disubstituted 2-Oxindoles Using Fluoroalkylsulfonyl Chlorides[J]. Org Lett,2014,16(17):4594-4597.
[12]	YANG Zhiyong. The Synthesis of Some Nitrogen Heterocyclic Compounds and Derivatives[D]. Changsha:Hu'nan University,2014(in Chinese). 杨志勇. 一些含氮杂环化合物及其衍生物的合成[D]. 长沙:湖南大学,2014.
[13]	Tang S,Zhou D,Wang Y. Metal-Free Meerwein Carboarylation of Alkenes with Anilines:A Straightforward Approach to 3-Benzyl-3-alkyloxindoles[J]. Eur J Org Chem,2014,2014(17):3656-3661.
[14]	Zhou D,Li Z H,Li J,et al.Copper-Catalysed Alkylarylation of Activated Alkenes Using AIBN and Beyond:An Access to Cyano-Containing Oxindoles[J]. Eur J Org Chem,2015,2015(7):1606-1612.
[15]	Tang S,Li S H,Zhou D,et al.Stereoselective C(sp3)-C(sp2) Negishi Coupling of (2-Amido-1-phenylpropyl) Zinc Compounds Through the Steric Control of β-Amido Group[J]. Sci China Chem,2013,56(9):1293-1300.
[16]	ZHOU Dong,LI Yuhua,DENG Youlin,et al.Recent Progress on Radical C—H Bond Cyclization to Form Oxindoles[J]. J Jishou Univ(Nat Sci Edn),2015,36(2):60-70(in Chinese). 周栋,李玉花,邓佑林,等. 自由基介导 C—H键环化合成吲哚酮的研究进展[J]. 吉首大学学报(自然科学版),2015,36(2):60-70.
[17]	Dai Q,Yu J,Jiang Y,et al.The Carbomethylation of Arylacrylamides Leading to 3-Ethyl-3-substituted Indolin-2-one by Cascade Radical Addition/Cyclization[J].Chem Commun,2014,50(29):3865-3867.

Metal-free Cyclization of Alkenes Toward Perfluorinated Oxindoles

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