Weijun Fu

Name:

Organization: Luoyang Normal University

Department: College of Chemistry and Chemical Engineering

Title:

Chemicals
References

Visible-light-induced photocatalytic difluoroacetylation of imidazopyridines via direct and regioselective CH functionalization

Co-reporter:Guojie Yin, Mei Zhu, Weijun Fu

Journal of Fluorine Chemistry 2017 Volume 199(Volume 199) pp:

Publication Date(Web):1 July 2017

DOI:10.1016/j.jfluchem.2017.04.005

•Direct and regioselective CH functionalization of imidazoheterocycles.•Visible-light-mediated direct and regioselective difluoroacetylation reaction.•C3-regioselective difluoroacetylation of imidazoheterocycles with high functional group tolerance.A visible-light-mediated direct and regioselective difluoroacetylation reaction of imidazoheterocycles by using BrCF2CO2Et under mild reaction conditions has been developed. With the utilization of a highly active CF2CO2Et radical, the developed photocatalytic method enables the introduction of a CF2CO2Et group in an efficient and regioselective reaction through CH bond functionalization with high functional group tolerance.C3-regioselective difluoroacetylation of imidazoheterocycles has been realized through visible-light-promoted radical addition under mild reaction conditions.Download high-res image (125KB)Download full-size image

Visible-light-mediated direct difluoromethylation of alkynoates: synthesis of 3-difluoromethylated coumarins

Co-reporter:Mei Zhu;Zhiqiang Wang;Chen Xu;Baoming Ji

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 43) pp:9057-9060

Publication Date(Web):2017/11/07

DOI:10.1039/C7OB02366A

A photoredox-catalyzed direct difluoromethylation of alkynoates has been developed. A well-designed photoredox system induces a single-step, regioselective installation of CF2H onto alkynes. Difluoromethyl sulfone was used as an easy to handle CF2H radical source to afford the desired 3-difluoromethylated coumarins in moderate to good yields via a radical-triggered tandem difluoromethylation/5-exo cyclization/ester migration process.

Synthesis of difluoromethylenephosphonated oxindoles through visible-vight-induced radical cyclization of N-arylacrylamides

Co-reporter:Guojie Yin, Mei Zhu, Gangbin Yang, Xuemeng Wang, Weijun Fu

Journal of Fluorine Chemistry 2016 Volume 191() pp:63-69

Publication Date(Web):November 2016

DOI:10.1016/j.jfluchem.2016.09.017

•Visible-light-induced difluoromethylenephosphonation of N-arylacrylamides.•Two new CC bonds were formed via a sequential radcial addition and cyclization process.•The reaction afforded difluoromethylenephosphonated oxindoles with good functional group tolerance.A general and efficient method for the synthesis of oxindole derivatives through visible-light-induced difluoromethylenephosphonation of N-arylacrylamides has been developed. The phosphonodifluoromethyl radicals, which is generated in situ from the corresponding BrCF2PO(OEt)2 under visible-light irradiation, in combination with N-arylacrylamides furnished difluoromethylenephosphonated oxindoles via a proposed tandem radical cyclization process. Notable advantages of this method include its simplicity and mild conditions, avoidance of toxic reagents, and compatibility with a variety of functional groups.Highly efficient approach to obtain CF2PO(OEt)2-containing oxindoles has been realized through visible-light-promoted aryldifluoromethylenephosphonation of N-arylacrylamides with BrCF2PO(OEt)2.

Regioselective 2,2,2-Trifluoroethylation of Imidazopyridines by Visible Light Photoredox Catalysis

Co-reporter:Mei Zhu, Xin Han, Weijun Fu, Zhiqiang Wang, Baoming Ji, Xin-Qi Hao, Mao-Ping Song, and Chen Xu

The Journal of Organic Chemistry 2016 Volume 81(Issue 16) pp:7282-7287

Publication Date(Web):June 22, 2016

DOI:10.1021/acs.joc.6b00950

A visible-light-induced C-3 selective trifluoroethylation of imidazoheterocycles using 1,1,1-trifluoro-2-iodoethane as trifluoroethyl radical sources was developed. The methodology enables the introduction of a trifluoroethyl group in a fast and efficient reaction under mild conditions with excellent regioselectivities and high functional group tolerance.

Visible-Light-Mediated Radical Aryldifluoroacetylation of Alkynes with Ethyl Bromodifluoroacetate for the Synthesis of 3-Difluoroacetylated Coumarins

Co-reporter:Weijun Fu, Mei Zhu, Guanglong Zou, Chen Xu, Zhiqiang Wang, and Baoming Ji

The Journal of Organic Chemistry 2015 Volume 80(Issue 9) pp:4766-4770

Publication Date(Web):April 3, 2015

DOI:10.1021/acs.joc.5b00305

A mild and efficient method for the synthesis of 3-difluoroacetylated coumarins through visible-light-promoted aryldifluoroacetylation of alkynes with ethyl bromodifluoroacetate has been developed. The reaction allows the direct formation of Csp2–CF2COOEt and C–C bonds via a proposed tandem radical cyclization process.

An approach to 6-trifluoromethyl-phenanthridines through visible-light-mediated intramolecular radical cyclization of trifluoroacetimidoyl chlorides

Co-reporter:Weijun Fu, Mei Zhu, Fengjuan Xu, Yuqin Fu, Chen Xu and Dapeng Zou

RSC Advances 2014 vol. 4(Issue 33) pp:17226-17229

Publication Date(Web):28 Mar 2014

DOI:10.1039/C4RA02384F

A mild and efficient visible light-mediated intramolecular radical cyclization of trifluoroacetimidoyl chlorides is developed for the synthesis of 6-(trifluoromethyl)phenanthridine derivatives. The reaction involves the generation of radical intermediates from C(sp2)–Cl bonds and a homolytic radical aromatic substitution (HAS) process.

Visible-Light-Mediated Radical Aryldifluoroacetylation of N-Arylacrylamides to give Difluoroacetylated Oxindoles

Co-reporter:Dr. Weijun Fu;Mei Zhu;Guanglong Zou;Chen Xu;Zhiqiang Wang

Asian Journal of Organic Chemistry 2014 Volume 3( Issue 12) pp:1273-1276

Publication Date(Web):

DOI:10.1002/ajoc.201402199

Abstract

A simple and practical approach to oxindole derivatives via visible-light-photocatalyzed aryldifluoroacetylation of N-arylacrylamides with BrCF₂CO₂Et has been developed. This method provides convenient access to a variety of difluoroester-substituted oxindoles under mild conditions.

A Metal-Free Route to CF3-Containing Oxindoles by PhI(OAc)2-Mediated Trifluoromethylation of N-Arylacrylamides with TMSCF3

Co-reporter:Weijun Fu;Fengjuan Xu;Yuqin Fu;Chen Xu;Shihui Li;Dapeng Zou

European Journal of Organic Chemistry 2014 Volume 2014( Issue 4) pp:709-712

Publication Date(Web):

DOI:10.1002/ejoc.201301512

Abstract

A mild and efficient PhI(OAc)₂-mediated trifluoromethylation reaction of N-arylacrylamides with TMSCF₃ under metal-free conditions was developed. This method provides convenient access to a variety of useful CF₃-containing oxindoles in moderate to good yields.

Palladium-catalyzed intramolecular C−H bond functionalization of trifluoroacetimidoyl chloride derivatives: Synthesis of 6-trifluoromethyl-phenanthridines

Co-reporter:Mei Zhu, Weijun Fu, Guanglong Zou, Chen Xu, Zhiqiang Wang

Journal of Fluorine Chemistry 2014 Volume 163() pp:23-27

Publication Date(Web):July 2014

DOI:10.1016/j.jfluchem.2014.04.005

•Palladium-catalyzed intramolecular cyclization of trifluoroacetimidoyl chlorides.•CSp2–CSp2 bonds formation via C–H bond functionalization.•The reaction afforded 6-trifluoromethyl-phenanthridines with good functional group tolerance.Highly efficient approaches to obtain 6-trifluoromethyl-phenanthridine derivatives have been realized through the palladium-catalyzed intramolecular C–H bond functionalization of trifluoroacetimidoyl chlorides. The reaction allows the direct formation of CSp2–CSp2 bonds via C–H bond functionalization and rapid access to phenanthridine ring systems in moderate to high yields with good functional group tolerance.Highly efficient approaches to obtain 6-trifluoromethyl-phenanthridine derivatives have been realized through the palladium-catalyzed intramolecular C−H bond functionalization of trifluoroacetimidoyl chlorides.

Visible-light-mediated trifluoroethylation of 2-isocyanobiaryl with trifluoroethyl iodide: Synthesis of 6-trifluoroethyl-phenanthridines

Co-reporter:Weijun Fu, Mei Zhu, Chen Xu, Guanglong Zou, Zhiqiang Wang, Baoming Ji

Journal of Fluorine Chemistry 2014 Volume 168() pp:50-54

Publication Date(Web):December 2014

DOI:10.1016/j.jfluchem.2014.08.022

•Visible-light-promoted trifluoroethylation of 2-isocyanobiaryl.•Two new CC bonds were formed via a sequential isocyanide insertion and homolytic aromatic substitution (HAS) process.•The reaction afforded 6-trifluoroethyl-phenanthridines with good functional group tolerance.A practical strategy has been described for the preparation of 6-trifluoroethyl-phenanthridine derivatives using a visible-light-promoted trifluoroethylation reaction of 2-isocyanobiaryl with trifluoroethyl iodide. These reactions could be carried out at room temperature in good to excellent chemical yields with good functional group tolerance.Highly efficient approach to obtain 6-trifluoroethyl-phenanthridine derivatives has been realized through visible-light-promoted trifluoroethylation of 2-isocyanobiaryl with trifluoroethyl iodide.

Efficient synthesis of 2-trifluoromethyl quinolines via base-assisted propargyl-allenyl isomerization and aza-electrocyclization of trifluoromethylated alkynyl imines

Co-reporter:Mei Zhu, Ziping Wang, Fengjuan Xu, Jiaqi Yu, Weijun Fu

Journal of Fluorine Chemistry 2013 Volume 156() pp:21-25

Publication Date(Web):December 2013

DOI:10.1016/j.jfluchem.2013.08.009

•Base-assisted electrocyclization of trifluoromethylated alkynyl imines.•The reaction via propargyl-allenyl isomerization and aza-electrocyclization.•The reaction afforded 2-trifluoromethylated quinolines in high yields.A mild and efficient base-mediated propargyl-allenyl isomerization and aza-electrocyclization reaction of trifluoromethylated alkynyl imines have been developed. This method provides a convenient access to 2-trifluoromethylated quinolines in high efficiency.A mild and efficient base-mediated propargyl-allenyl isomerization and aza-electrocyclization reaction of trifluoromethylated alkynyl imines have been developed. This method provides a convenient access to 2-trifluoromethylated quinolines in high efficiency.

Synthesis of 3,3-Disubstituted Oxindoles by Visible-Light-Mediated Radical Reactions of Aryl Diazonium Salts with N-Arylacrylamides

Co-reporter:Weijun Fu, Fengjuan Xu, Yuqin Fu, Mei Zhu, Jiaqi Yu, Chen Xu, and Dapeng Zou

The Journal of Organic Chemistry 2013 Volume 78(Issue 23) pp:12202-12206

Publication Date(Web):October 16, 2013

DOI:10.1021/jo401894b

A mild and efficient visible-light-mediated diarylation of N-arylacrylamides with aryl diazonium salts under mild conditions has been developed. This method provides convenient access to a variety of useful 3,3-disubstituted oxindoles by constructing two C–C bonds in one step.

Highly Efficient Synthesis of Multisubstituted Furans through Cupric Halide-Mediated Intramolecular Halocyclization of 1-(1-Alkynyl)cyclopropyl Ketones

Co-reporter:Mei Zhu;Wei-Jun Fu;Chen Xu;Guang-Long Zou;Zhi-Qiang Wang;Bao-Ming Ji

European Journal of Organic Chemistry 2012 Volume 2012( Issue 24) pp:4609-4615

Publication Date(Web):

DOI:10.1002/ejoc.201200601

Abstract

A convenient and efficient method for the synthesis of 3-halofurans was developed by using a cascade reaction between 1-(1-alkynyl)cyclopropyl ketones and cupric halide. Under mild reaction conditions, both 3-chloro- and 3-bromofuran derivatives were obtained in high yields. The reaction involves consecutive multiple bond formations, includingC–O and C–Br bonds, with high regioselectivity. Mechanistic aspects are described.

An efficient synthesis of 2-trifluoromethyl quinolines via gold-catalyzed cyclization of trifluoromethylated propargylamines

Co-reporter:Mei Zhu, Weijun Fu, Guanglong Zou, Chen Xun, Dongsheng Deng, Baoming Ji

Journal of Fluorine Chemistry 2012 Volume 135() pp:195-199

Publication Date(Web):March 2012

DOI:10.1016/j.jfluchem.2011.11.002

A highly efficient cyclization reaction of trifluoromethylated propargylamines leading to 2-trifluoromethyl-4-aryl quinolines was developed by using gold(I) as a catalyst under extremely mild conditions.Graphical abstractA highly efficient cyclization reaction of trifluoromethylated propargylamines leading to 2-trifluoromethyl-4-aryl quinolines was developed by using gold(I) as a catalyst under extremely mild conditions.Highlights► Gold-catalyzed cyclization of trifluoromethylated propargylamines. ► Various 1-trifluoromethylpropargylamines are viable substrates. ► The reaction mechanism is suggested to involve cyclization-oxidation.

Selective trifluoromethylation and alkynylation of tetrahydroisoquinolines using visible light irradiation by Rose Bengal

Co-reporter:Weijun Fu, Wenbo Guo, Guanglong Zou, Chen Xu

Journal of Fluorine Chemistry 2012 140() pp: 88-94

Publication Date(Web):

DOI:10.1016/j.jfluchem.2012.05.009

An efficient synthesis of ring-fused indoles via copper-catalyzed tandem reaction of N-(o-alkynylphenyl)imines

Co-reporter:Weijun Fu;Mei Zhu;Guanglong Zou

Applied Organometallic Chemistry 2010 Volume 24( Issue 7) pp:499-502

Publication Date(Web):

DOI:10.1002/aoc.1648

Abstract

A copper-catalyzed tandem intramolecular cyclization-addition reaction of N-(o-alkynylphenyl)imines is disclosed. This strategy offers a simple and promising method for accessing ring-fused indoles. Copyright © 2010 John Wiley & Sons, Ltd.

Visible-light-mediated radical oxydifluoromethylation of olefinic amides for the synthesis of CF2H-containing heterocycles

Co-reporter:Weijun Fu, Xin Han, Mei Zhu, Chen Xu, Zhiqiang Wang, Baoming Ji, Xin-Qi Hao and Mao-Ping Song

Chemical Communications 2016 - vol. 52(Issue 91) pp:NaN13416-13416

Publication Date(Web):2016/10/28

DOI:10.1039/C6CC07771D

The visible-light-mediated oxydifluoromethylation of olefinic amides with difluoromethyl sulfones has been explored. This method allows for an efficient and practical synthesis of a variety of CF2H-containing benzoxazines and oxazolines bearing various functional groups under mild conditions.