Co-reporter:Haiyong Zhao;Xiaoqiu Pu;Xianjin Yang
Chinese Journal of Chemistry 2017 Volume 35(Issue 9) pp:1417-1421
Publication Date(Web):2017/09/01
DOI:10.1002/cjoc.201700114
A novel method for the synthesis of 2-chloro enesulfonamides via the one-pot addition-elimination of N-chloro-N-fluorobenzenesulfonamides (CFBSA) to styrenes in the presence of Et3N is described. A total of 20 examples are presented to illustrate this concept including various of styrenes.
Co-reporter:Xiao-Hui Hu, Xiao-Qiu Pu, Rui Liu, Chun-Xiao Cui, Jun Yang and Xian-Jin Yang
RSC Advances 2016 vol. 6(Issue 63) pp:58613-58616
Publication Date(Web):03 Jun 2016
DOI:10.1039/C6RA06840E
A facile access to cis-dihydrofurobenzofuran from a Pd-catalyzed intramolecular oxidative C–O bond formation of 2-(2,5-dihydro-furan-2-yl)-phenol is reported. The combined use of Pd(OAc)2 as catalyst, acetonitrile as solvent and AgOAc or air as oxidant affords cis-dihydrofurobenzofurans in good (up to 83%) yields.
Co-reporter:Zehai Lu, Qingwei Li, Minghua Tang, Panpan Jiang, Hao Zheng and Xianjin Yang
Chemical Communications 2015 vol. 51(Issue 80) pp:14852-14855
Publication Date(Web):11 Aug 2015
DOI:10.1039/C5CC05052A
A structurally simple, highly reactive chlorinating reagent, N-chloro-N-fluorobenzenesulfonylamine (CFBSA), was conveniently prepared from inexpensive Chloramine B in high yield. A wide range of substrates were chlorinated with it to obtain products in good to high yields and appropriate selectivity.
Co-reporter:Rui Liu, Ze-Hai Lu, Xiao-Hui Hu, Jun-Li Li, and Xian-Jin Yang
Organic Letters 2015 Volume 17(Issue 6) pp:1489-1492
Publication Date(Web):March 12, 2015
DOI:10.1021/acs.orglett.5b00376
A novel and practical reaction for the direct intramolecular oxidative coupling of butenylated arenes is reported. With the catalysis of Pd(OAc)2, reactions of various butenylated arenes and carboxylic acids with Selectfluor reagent in CH3CN solution afforded the corresponding monocarboxylation/cyclization products in good yields under mild conditions. This research demonstrated an economic method with the synthesis of 2-tetralyl carboxylic esters, a valuable class of bioactive compounds.
Co-reporter:Wenhua Zhu;Xiaohui Hu;Fajie Wang;Xianjin Yang;Xinyan Wu
Chinese Journal of Chemistry 2015 Volume 33( Issue 2) pp:220-224
Publication Date(Web):
DOI:10.1002/cjoc.201400680
Abstract
The direct preparation of a kind of fluorinating reagent 1 [F-TEDA-N(SO2Ph)2] was realized in high yield via the complexation of N-fluorobenzenesulfonimide (NFSI) with 1-(chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium N′,N′-bis-(benzenesulfonylimide) salt. In its fluorination to oxindoles, the fluorinating products 6 were afforded in moderate to high yields.
Co-reporter:Fajie Wang;Juli Li;Qingyang Hu;Xianjin Yang;Xin-Yan Wu;Haoming He
European Journal of Organic Chemistry 2014 Volume 2014( Issue 17) pp:3607-3613
Publication Date(Web):
DOI:10.1002/ejoc.201402072
Abstract
We describe our attempts to fine-tune the reactivity and selectivity of N-fluorobenzenesulfonamide in fluorination reactions by changing the substituents on its phenyl rings. A series of N-fluorobenzenesulfonamides bearing substituents at the ortho, meta, and para positions were prepared, and were used in the enantioselective fluorination of 2-oxindoles catalysed by chiral palladium complexes. Fluorinating reagents 1b, 1c, 1d, 1e, 1h, 1i, and 1j gave similar results to 1a, while 1f, 1g, and 1n gave worse yields and selectivities. Under mild reaction conditions, a series of 3-fluoro-2-oxindoles were obtained in excellent yields (up to 98 %) and enantioselectivities (up to 99 % ee) using N-fluoro-4,4′-difluoro-benzenesulfonamide as the fluorination agent.
Co-reporter:Chun-Xiao Cui, Hui Li, Xian-Jin Yang, Jun Yang, and Xiao-Qiang Li
Organic Letters 2013 Volume 15(Issue 23) pp:5944-5947
Publication Date(Web):November 14, 2013
DOI:10.1021/ol402782f
A series of functionalized 2,5-dihydrofurans were efficiently synthesized via an amine-promoted Petasis borono–Mannich reaction of 4-substituted 1,2-oxaborol-2(5H)-ols with salicylaldehydes in high yields. The process, which combines a boronic acid-based Mannich reaction and a highly efficient intramolecular SN2 cyclization, provides a one-step and efficient route toward 2,5-dihydrofurans from simple and stable starting materials.
Co-reporter:Hao-Ming He, Lei Gao, Xian-Jin Yang, Wei-hong Guo, Hui Li, Tian Xie, San-Ke Yang, Jiang-Ping Wang, Yan Zhang, Xue-Yan Yang
Journal of Fluorine Chemistry 2013 Volume 156() pp:158-163
Publication Date(Web):December 2013
DOI:10.1016/j.jfluchem.2013.10.003
•The polypropylene/polydimethylsiloxane/graphite fluoride (PP/PDMS/GF) composites are prepared.•The study of superhydrophobicity showed that the WCA reaches 148° with a sliding angle 6°.•Sandpapering and addition of GF can apparently increase superhydrophobicity.The polypropylene/polydimethylsiloxane/graphite fluoride (PP/PDMS/GF) composites are prepared with dynamic curing technology by simple blending of polypropylene, graphite fluoride and polydimethylsiloxane, and then their superhydrophobic properties are investigated. The results indicates that the static WCA reaches 148° with a sliding angle 6° for surface sandpapered PP/PDMS/GF = 100/20/15 composite, which supplies a much economical and convenient method for preparing superhydrophobic materials.The polypropylene/polydimethylsiloxane/graphite fluoride (PP/PDMS/GF) composites are prepared with dynamic curing technology by the simple blending of polypropylene, graphite fluoride and polydimethylsiloxane. The superhydrophobicity investigation indicates that the static WCA reaches 148° with a sliding angle 6° for surface sandpapered PP/PDMS/GF = 100/20/15 composite.
Co-reporter:Haoming He, Lei Gao, Xianjin Yang, Qingyang Hu, Yan Zhang, Guanlong Chen, Jiangping Wang, Sanke Yang, Tian Xie, Weihong Guo
Journal of Fluorine Chemistry 2013 Volume 151() pp:32-37
Publication Date(Web):July 2013
DOI:10.1016/j.jfluchem.2013.04.004
•The surface fluorinated polypropylene particles/polypropylene blends were prepared.•Their mechanical and thermodynamic properties varied with the ratio of SFPP/PP.•The blending of regular SFPP/PP particle improved its impact strength and flexural strength.The surface fluorinated polypropylene and PP (SFPP/PP) blend was obtained by direct fluorination of polypropylene particle with 3% F2/N2 gas and subsequent blending with polypropylene particle. The analyses indicated that the mechanical and thermodynamic properties of SFPP/PP blends such as tensile strength, impact strength, flexural strength, and cooling crystallization characteristics varied with the ratio of SFPP/PP. With the increase of SFPP in the blend, the tensile strength was decreased, while the impact strength and flexural strength might be improved. Meanwhile, fluorination resulted in the rise of melting point of PP. and in the DSC plot of SFPP/PP, annealing made the melting single peak split into double peak, which demonstrated that SFPP and PP were compatible but instable.The surface fluorinated polypropylene and PP (SFPP/PP) blend was obtained by direct fluorination of polypropylene particle with 3% F2/N2 gas and subsequent blending with polypropylene particle. The analyses indicated that the mechanical and thermodynamic properties of SFPP/PP blends such as tensile strength, impact strength, flexural strength, and cooling crystallization characteristics varied with the ratio of SFPP/PP. With the increase of SFPP in the blend, the tensile strength was decreased, while the impact strength and flexural strength might be improved. Meanwhile, fluorination resulted in the rise of melting point of PP. And in the DSC plot of SFPP/PP, annealing made the melting single peak split into double peak, which demonstrated that SFPP and PP were compatible but instable.
Co-reporter:Yan Zhang, Xian-Jin Yang, Tian Xie, Guan-Long Chen, Wen-Hua Zhu, Xiao-Qi Zhang, Xue-Yan Yang, Xin-Yan Wu, Xiao-Peng He, Hao-Ming He
Tetrahedron 2013 69(24) pp: 4933-4937
Publication Date(Web):
DOI:10.1016/j.tet.2013.04.037
Co-reporter:Qi Wang, Feng Huan, Haiming Shen, Ji-Chang Xiao, Min Gao, Xianjin Yang, Shun-Ichi Murahashi, Qing-Yun Chen, and Yong Guo
The Journal of Organic Chemistry 2013 Volume 78(Issue 24) pp:12525-12531
Publication Date(Web):November 19, 2013
DOI:10.1021/jo402212j
CF3-containing esters smoothly reacted with electron-deficient alkenes in the presence of a phosphine (2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl) organocatalyst at room temperature in an aerobic atmosphere. These Michael reactions efficiently provided products with a CF3 quaternary carbon center.
Co-reporter:Guanlong Chen, Fuli Chen, Yan Zhang, Xueyan Yang, Xiaoming Yuan, Fanhong Wu, Xianjin Yang
Journal of Fluorine Chemistry 2012 Volume 133() pp:155-159
Publication Date(Web):January 2012
DOI:10.1016/j.jfluchem.2011.10.012
This paper studied the fluorination reaction of p-substituted benzenesulfonimides with diluted elemental fluorine to synthesize N-fluoro-benzenesulfonimide (NFSI) analogues. Several synthetic methods were compared and we found that, for many p-substituted benzenesulfonimides, the fluorination of their sodium salts with 10% F2–N2 mixed gas in acetonitrile at room temperature could afford NFSI analogues in moderate to good yields.Graphical abstractThe fluorination of the sodium salts of p-substituted benzenesulfonimide with 10% F2–N2 mixed gas in acetonitrile at room temperature could afford the corresponding N-fluoro-benzenesulfonimide (NFSI) analogues in moderate to good yields.Highlights► Developing method for the synthesis of N–F reagents is useful. ► An efficient procedure for the synthesis of NFSI analogues was realized. ► The p-substituted NFSI analogues were afforded in moderate to good yields.
Co-reporter:Xiao-Ming Yuan, Jian Xu, Zhen-Jiang Liu, Xian-Jin Yang, Li-Min Wang, Yan Zhang, Xue-Yan Yang, Xiao-Peng He, Jin-Tao Liu
Journal of Fluorine Chemistry 2012 Volume 144() pp:102-107
Publication Date(Web):December 2012
DOI:10.1016/j.jfluchem.2012.07.017
The stereoselectivity of the reaction of (Rs)-trifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketimines with TMSCN was studied. The diastereomers of α-trifluoromethyl unsaturated cyano amines were obtained, respectively, in good yields with excellent diastereoselectivities in terms of the different solvents used. In c-hexane, the (S, Rs)-isomer was obtained with up to 17:1 dr, whereas the (R, Rs)-isomer was generated as the main product with up to 145:1 dr in DMF at −60 °C.Graphical abstractThe stereoselectivity of the reaction of (Rs)-trifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketimines with TMSCN was studied. The diastereomers of α-trifluoromethyl unsaturated cyano amines were obtained, respectively, in good yields with excellent diastereoselectivities in terms of the different solvents used. In c-hexane, the (S, Rs)-isomer was obtained with up to 17:1 dr, whereas the (R, Rs)-isomer was generated as the main product with up to 145:1 dr in DMF at −60 °C.Highlights► The reaction of chiral N-tert-butanesulfinyl ketimines with TMSCN was studied. ► Different diastereoselectivities were obtained in terms of the solvents used. ► In c-hexane, d.r. (2a:3a) of the addition products is up to 1:17. ► In DMF, a reversed diastereoselectivity was observed with up to 145:1 d.r. (2a:3a).
Co-reporter:Weihong Guo, Lei Gao, Guanlong Chen, Yan Zhang, Haoming He, Tian Xie, Sanke Yang, Shimin Ding, Xianjin Yang
Journal of Fluorine Chemistry 2012 Volume 144() pp:182-188
Publication Date(Web):December 2012
DOI:10.1016/j.jfluchem.2012.09.011
The surface fluorinated polypropylene/polypropylene blend (SFPP/PP) was obtained by direct fluorination of polypropylene particle with 3% F2/N2 gas and subsequently blending it with polypropylene particle and antioxidant 1010. The nonisothermal crystallization kinetics properties of SFPP/PP were investigated using differential scanning calorimetry and the results indicated the compatibility of SFPP/PP is good, the crystallization temperature T0, Tc and crystallization activation energy ΔE are increased, whereas enthalpy ΔHc are decreased with the incorporation of fluorine to PP. Several macrokinetic models such as Jeziorny, Ozawa and Mo are used to analyze the nonisothermal crystallization behavior of the blend, among which Mo equation supplies a convenient and reasonable kinetic approach to describe its crystallization process.Graphical abstractHighlights► The surface fluorinated polypropylene/PP blend was prepared. ► The nonisothermal crystallization kinetics properties of the blend were studied. ► DSC shows the incompatibility of surface fluorinated polypropylene and PP is good. ► Introducing fluorine into PP leads to its T0, Tc and ΔE increasing. ► Mo equation supplies a reasonable description for its crystallization behavior.
Co-reporter:Yaoping Zhu, Xueyan Yang, Xiang Fang, Xianjin Yang, LingLing Ye, Wei Cai, Yan Zhang, Fanhong Wu
Tetrahedron 2011 67(6) pp: 1251-1257
Publication Date(Web):
DOI:10.1016/j.tet.2010.11.090
Co-reporter:Xueyan Yang;Dr. Xianjin Yang;Shengjie Zhu;Lingling Ye;Yang Chen;Guanlong Chen; Dr. Fanhong Wu
Chinese Journal of Chemistry 2010 Volume 28( Issue 11) pp:2269-2273
Publication Date(Web):
DOI:10.1002/cjoc.201090375
Abstract
4-Fluoroalkyl-2-acylamino-4-butyrolactones were afforded in moderate yields by the sodium dithionite initiated one-pot addition-lactonization reaction of polyfluoroalkyl iodides with 2-acylamino-4-pentenoic acids.
Co-reporter:Jian Xu, Zhen-Jiang Liu, Xian-Jin Yang, Li-Min Wang, Guan-Long Chen, Jin-Tao Liu
Tetrahedron 2010 66(46) pp: 8933-8937
Publication Date(Web):
DOI:10.1016/j.tet.2010.09.047
Co-reporter:Xueyan Yang, Xianjin Yang, Wei Pan, Ying Wang, Wei Cai, Fanhong Wu
Tetrahedron 2010 66(36) pp: 7288-7294
Publication Date(Web):
DOI:10.1016/j.tet.2010.07.002
Co-reporter:Zehai Lu, Qingwei Li, Minghua Tang, Panpan Jiang, Hao Zheng and Xianjin Yang
Chemical Communications 2015 - vol. 51(Issue 80) pp:NaN14855-14855
Publication Date(Web):2015/08/11
DOI:10.1039/C5CC05052A
A structurally simple, highly reactive chlorinating reagent, N-chloro-N-fluorobenzenesulfonylamine (CFBSA), was conveniently prepared from inexpensive Chloramine B in high yield. A wide range of substrates were chlorinated with it to obtain products in good to high yields and appropriate selectivity.