Iron-catalyzed tandem cyclization of olefinic dicarbonyl compounds with benzylic Csp3–H bonds for the synthesis of dihydrofurans

Li-Na Guo; Shun Wang; Xin-Hua Duan; Shi-Liu Zhou

doi:10.1039/c5cc00426h

Iron-catalyzed tandem cyclization of olefinic dicarbonyl compounds with benzylic Csp3–H bonds for the synthesis of dihydrofurans

Chemical Communications ◽

10.1039/c5cc00426h ◽

2015 ◽

Vol 51 (23) ◽

pp. 4803-4806 ◽

Cited By ~ 45

Author(s):

Li-Na Guo ◽

Shun Wang ◽

Xin-Hua Duan ◽

Shi-Liu Zhou

Keyword(s):

Radical Cyclization ◽

Quaternary Carbon ◽

Dicarbonyl Compounds ◽

Ready Access ◽

Tandem Cyclization

A novel iron-catalyzed radical cyclization of olefinic dicarbonyl compounds with benzyl hydrocarbons and simple alkanes has been developed. This protocol provides ready access to a variety of dihydrofurans containing a quaternary carbon center in moderate to good yields.

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Construction of a chiral quaternary carbon center by a radical cyclization/ring-enlargement reaction: synthesis of 4α-azidoethyl carbocyclic ribose, a key unit for the synthesis of cyclic ADP-ribose derivatives of biological importance

Tetrahedron ◽

10.1016/j.tet.2015.05.084 ◽

2015 ◽

Vol 71 (33) ◽

pp. 5407-5413 ◽

Cited By ~ 4

Author(s):

Takatoshi Sato ◽

Takayoshi Tsuzuki ◽

Satoshi Takano ◽

Kohtaro Kato ◽

Hayato Fukuda ◽

...

Keyword(s):

Radical Cyclization ◽

Reaction Synthesis ◽

Quaternary Carbon ◽

Ring Enlargement ◽

Biological Importance ◽

Cyclic Adp Ribose ◽

Derivatives Of

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ChemInform Abstract: Synthesis of Dihydropyrans and Dihydrofurans via Radical Cyclization of Unsaturated Alcohols and 1,3-Dicarbonyl Compounds

ChemInform ◽

10.1002/chin.201444099 ◽

2014 ◽

Vol 45 (44) ◽

pp. no-no

Author(s):

Hakan Aslan ◽

Deniz E. Akpinar ◽

Atilla Oektemer ◽

Mehtap Yakut ◽

Oguzhan Alagoez

Keyword(s):

Radical Cyclization ◽

Dicarbonyl Compounds ◽

Unsaturated Alcohols

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ChemInform Abstract: Iron-Catalyzed Tandem Cyclization of Olefinic Dicarbonyl Compounds with Benzylic Csp3-H Bonds for the Synthesis of Dihydrofurans.

ChemInform ◽

10.1002/chin.201529142 ◽

2015 ◽

Vol 46 (29) ◽

pp. no-no

Author(s):

Li-Na Guo ◽

Shun Wang ◽

Xin-Hua Duan ◽

Shi-Liu Zhou

Keyword(s):

Dicarbonyl Compounds ◽

Tandem Cyclization

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Synthesis of Seleno Oxindoles via Iodine-induced Radical Cyclization of N-arylacrylamides with Diorganyl Diselenides

Synthesis ◽

10.1055/a-1739-5042 ◽

2022 ◽

Author(s):

Hongmei Jiang ◽

Haicheng Shen ◽

Cehua Li ◽

Zheng Jin ◽

Yanxue Shang ◽

...

Keyword(s):

Radical Cyclization ◽

Cascade Cyclization ◽

Diphenyl Disulfide ◽

Radical Cascade ◽

Tandem Cyclization

A mild radical cascade cyclization of N-arylacrylamides with diselenides for the preparation of oxindoles via iodine oxidation is disclosed, which provide an eco-friendly process for the construction of C–Se bond. 25 Examples of N-arylacrylamide substrates were investigated with excellent yields. Besides, the tandem cyclization of acrylamide with diphenyl disulfide was also applicable under the same condition.

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ChemInform Abstract: Synthesis of Dihydrofurans Containing Trifluoromethyl Ketone and Heterocycles by Radical Cyclization of Fluorinated 1,3-Dicarbonyl Compounds with 2-Thienyl and 2-Furyl Substituted Alkenes.

ChemInform ◽

10.1002/chin.201210097 ◽

2012 ◽

Vol 43 (10) ◽

pp. no-no

Author(s):

Mehmet Yilmaz

Keyword(s):

Radical Cyclization ◽

Dicarbonyl Compounds

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ChemInform Abstract: Radical Cyclization to the Trifluoromethyl-Substituted Double Bond: Regioselectivity and Tandem Cyclization.

ChemInform ◽

10.1002/chin.198950074 ◽

1989 ◽

Vol 20 (50) ◽

Author(s):

T. MORIKAWA ◽

T. NISHIWAKI ◽

Y. KOBAYASHI

Keyword(s):

Double Bond ◽

Radical Cyclization ◽

Tandem Cyclization

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Radical Cyclization of Fluorinated 1,3-Dicarbonyl Compounds with Dienes Using Manganese(III) Acetate and Synthesis of Fluoroacylated 4,5-Dihydrofurans

Helvetica Chimica Acta ◽

10.1002/hlca.201100105 ◽

2011 ◽

Vol 94 (11) ◽

pp. 2027-2038 ◽

Cited By ~ 10

Author(s):

Mehmet Yılmaz ◽

E. Vildan Burgaz Yılmaz ◽

A. Tarık Pekel

Keyword(s):

Radical Cyclization ◽

Dicarbonyl Compounds

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Potassium Persulfate Mediated Oxidative Radical Cyclization of 1,3-Dicarbonyl Compounds with Styrenes for the Synthesis of Dihydrofurans

Synthesis ◽

10.1055/s-0034-1378806 ◽

2015 ◽

Vol 47 (20) ◽

pp. 3191-3197 ◽

Cited By ~ 8

Author(s):

Li-Na Guo ◽

Shun Wang ◽

Lin-Ye He

Keyword(s):

Radical Cyclization ◽

Potassium Persulfate ◽

Dicarbonyl Compounds ◽

Oxidative Radical Cyclization

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α-Sulfonyloxylation of 1,3-dicarbonyl compounds utilizing hypervalent iodine(iii) reagent: Construction of quaternary carbon center

Synthetic Communications ◽

10.1080/00397911.2018.1472281 ◽

2018 ◽

Vol 48 (15) ◽

pp. 1957-1965 ◽

Cited By ~ 1

Author(s):

Ruojuan Liu ◽

Junzheng Wang ◽

Wen Hu ◽

Xiaohui Zhang ◽

Yan Xiong

Keyword(s):

Hypervalent Iodine ◽

Quaternary Carbon ◽

Dicarbonyl Compounds

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Tandem SN2′ nucleophilic substitution/oxidative radical cyclization of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds

Organic & Biomolecular Chemistry ◽

10.1039/c7ob00620a ◽

2017 ◽

Vol 15 (15) ◽

pp. 3239-3247 ◽

Cited By ~ 3

Author(s):

Zhen Zhang ◽

Cheng Li ◽

Shao-Hua Wang ◽

Fu-Min Zhang ◽

Xue Han ◽

...

Keyword(s):

Nucleophilic Substitution ◽

Radical Cyclization ◽

Allylic Alcohols ◽

Dicarbonyl Compounds ◽

Oxidative Radical Cyclization

Herein we present a novel tandem SN2′ nucleophilic substitution/oxidative radical cyclization of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds.

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