An Imidazole-functionalized Dioxovanadium Complex with the Highly Selective Oxidation of Sulfides
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摘要
A novel imidazole-functionalized dioxovanadium complex [V_2O_2(C_2O_4)(aIM)_4](aIM = 1-allylimidazole) was synthesized by the reaction of VO(acac)_2 with 1-allylimidazole and fully characterized by single-crystal X-ray diffraction(SCXRD),powder X-ray diffraction(PXRD),X-ray photoelectron spectroscopy(XPS),Fourier transform infrared spectroscopy(FT-IR) and elemental analyses. Interestingly,the oxalate was in-situ generated from the acetylacetone anion of VO(acac)_2 and further coordinated with the vanadium cation and finally complex 1 was achieved. The crystal of complex 1 belongs to the monoclinic system,space group P2_1/n with a = 10.7922(9),b = 10.6296(8),c = 13.2936(11) ?,μ = 0.677 mm~(-1),M_r = 686.48,V = 1516.9(2) ?~3,Z = 2,D_c = 1.503 g/cm~3,F(000) = 708,R = 0.0543,and wR = 0.1517 for 2459 observed reflections with I > 2σ(I). Notably,complex 1 is further used as catalyst in the oxidation of sulfides using H_2O_2 as the oxidant and exhibits excellent catalytic performance(conv. up to 95.6%,sele. up to 98.9%).
A novel imidazole-functionalized dioxovanadium complex [V_2O_2(C_2O_4)(aIM)_4](aIM = 1-allylimidazole) was synthesized by the reaction of VO(acac)_2 with 1-allylimidazole and fully characterized by single-crystal X-ray diffraction(SCXRD),powder X-ray diffraction(PXRD),X-ray photoelectron spectroscopy(XPS),Fourier transform infrared spectroscopy(FT-IR) and elemental analyses. Interestingly,the oxalate was in-situ generated from the acetylacetone anion of VO(acac)_2 and further coordinated with the vanadium cation and finally complex 1 was achieved. The crystal of complex 1 belongs to the monoclinic system,space group P2_1/n with a = 10.7922(9),b = 10.6296(8),c = 13.2936(11) ?,μ = 0.677 mm~(-1),M_r = 686.48,V = 1516.9(2) ?~3,Z = 2,D_c = 1.503 g/cm~3,F(000) = 708,R = 0.0543,and wR = 0.1517 for 2459 observed reflections with I > 2σ(I). Notably,complex 1 is further used as catalyst in the oxidation of sulfides using H_2O_2 as the oxidant and exhibits excellent catalytic performance(conv. up to 95.6%,sele. up to 98.9%).
A novel imidazole-functionalized dioxovanadium complex [V_2O_2(C_2O_4)(aIM)_4](aIM = 1-allylimidazole) was synthesized by the reaction of VO(acac)_2 with 1-allylimidazole and fully characterized by single-crystal X-ray diffraction(SCXRD),powder X-ray diffraction(PXRD),X-ray photoelectron spectroscopy(XPS),Fourier transform infrared spectroscopy(FT-IR) and elemental analyses. Interestingly,the oxalate was in-situ generated from the acetylacetone anion of VO(acac)_2 and further coordinated with the vanadium cation and finally complex 1 was achieved. The crystal of complex 1 belongs to the monoclinic system,space group P2_1/n with a = 10.7922(9),b = 10.6296(8),c = 13.2936(11) ?,μ = 0.677 mm~(-1),M_r = 686.48,V = 1516.9(2) ?~3,Z = 2,D_c = 1.503 g/cm~3,F(000) = 708,R = 0.0543,and wR = 0.1517 for 2459 observed reflections with I > 2σ(I). Notably,complex 1 is further used as catalyst in the oxidation of sulfides using H_2O_2 as the oxidant and exhibits excellent catalytic performance(conv. up to 95.6%,sele. up to 98.9%).
引文
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(13)Zhao,W.;Yang,C.;Cheng,Z.;Zhang,Z.A reusable catalytic system for sulfide oxidation and epoxidation of allylic alcohols in water catalyzed by poly(dimethyl diallyl)ammonium/polyoxometalate.Green Chem.2016,18,995-998.
(14)Li,Z.;Schweitzer,N.M.;League,A.B.;Bernales,V.;Peters,A.W.;Getsoian,A.B.;Wang,T.C.;Miller,J.T.;Vjunov,A.;Fulton,J.L.;Lercher,J.A.;Cramer,C.J.;Gagliardi,L.;Hupp,J.T.;Farha,O.K.Sintering-resistant single-site nickel catalyst supported by metal–organic framework.J.Am.Chem.Soc.2016,138,1977-1982.
(15)Fernández,I.;Khiar,N.Recent developments in the synthesis and utilization of chiral sulfoxides.Chem.Rev.2003,103,3651-3705.
(16)Amini,M.;Naslhajian,H.;Morteza,S.;Farnia,F.;Ho?yńska,M.Selective oxidation of sulfides catalyzed by the nanocluster polyoxomolybdate(NH4)12[Mo36(NO)4O108(H2O)16].Eur.J.Inorg.Chem.2015,23,3873-3878.
(17)Salgaonkar,P.D.;Shukla,V.G.;Akamanchi,K.G.Iodic acid(HIO3)in combination with tetraethylammonium bromide as a catalyst for selective and accelerated sulfoxidation.Synth.Commun.2005,35,2805-2810.
(18)Kamata,K.;Yonehara,K.;Sumida,Y.;Yamaguchi,K.;Hikichi,S.;Mizuno,N.Efficient epoxidation of olefins with≥99%selectivity and use of hydrogen peroxide.Science 2003,300,964-966.
(19)Yadav,M.;Bhunia,A.;Jana,S.K.;Roesky,P.W.Manganese-and lanthanide-based 1D chiral coordination polymers as an enantioselective catalyst for sulfoxidation.Inorg.Chem.2016,55,2701-2708.
(20)Nikoorazm,M.;Ghorbani-Choghamarani,A.;Noori,N.Oxo-vanadium(IV)Schiff base complex supported on modified MCM-41:a reusable and efficient catalyst for the oxidation of sulfides and oxidative S-S coupling of thiols.Appl.Organomet.Chem.2015,29,328-333.
(21)Zeng,Q.;Gao,Y.;Dong,J.;Weng,W.;Zhao,Y.Vanadium-catalyzed enantioselective oxidation of allyl sulfides.Tetrahedron:asymmetry 2011,22,717-721.
(2)Gazi,S.;Ng,W.K.H.;Ganguly,R.;Moeljadi,A.M.P.;Hirao,H.;Soo,H.S.Selective photocatalytic C–C bond cleavage under ambient conditions with earth abundant vanadium complexes.Chem.Sci.2015,6,7130-7142.
(3)Proust,A.;Thouvenot,R.;Gouzerh,P.Functionalization of polyoxometalates:towards advanced applications in catalysis and materials science.Chem.Commun.2008,16,1837-1852.
(4)Chen,B.;Huang,X.;Wang,B.;Lin,Z.;Hu,J.;Chi,Y.;Hu,C.Three new imidazole-functionalized hexanuclear oxidovanadium clusters with exceptional catalytic oxidation properties for alcohols.Chem.Eur.J.2013,19,4408-4413.
(5)Sheldrick,G.M.SHELXS-97,Program for X-ray Crystal Structure Solution.University of G?ttingen,Germany 1997.
(6)Brese,N.E.;O’Keeffe,M.Bond-valence parameters for solids.Acta Crystallogr.Sect.B 1991,47,192-197.
(7)Hopfengartner,G.;Borgmann,D.;Rademacher,I.;Wedler,G.;Hums,E.;Spitznagel,G.W.XPS studies of oxidic model catalysts Internal standards and oxidation numbers.J.Electron Spectrosc.Relat.Phenom.1993,63,91-116.
(8)Li,J.K.;Xu,Y.Q.;Hu,C.W.In situ synthesis of a novel dioxidovanadium-based nickel complex as catalyst for deep oxidative desulfurization with molecular oxygen.Inorg.Chem.Commun.2015,60,12-14.
(9)Bazhina,E.S.;Aleksandrov,G.G.;Efimov,N.N.;Ugolkova,E.A.;Minin,V.V.;Sidorov,A.A.;Novotortsev,V.M.;Eremenko,I.L.Synthesis,structure,and ESR spectra of the new heteronuclear complex{Li4(VO)2[(OOC)2C(H)Bu]4(H2O)8}·H2O.Russ.Chem.Bull.2013,62,962-965.
(10)Chen,C.;Sun,Q.;Ren,D.X.;Zhang,R.;Bai,F.Y.;Xing,Y.H.;Shi,Z.Bromoperoxidase mimic as catalysts for oxidative bromination-synthesis,structures and properties of the diversified oxidation state of vanadium(III,IV and V)complexes with pincer N-heterocycle ligands.Cryst Eng Comm.2013,15,5561-5573.
(11)Süss-Fink,G.;Stanislas,S.;Shul'pin,G.B.;Nizova,G.V.;Stoeckli-Evans,H.;Neels,A.;Bobillier,C.;Claude,S.Oxidative functionalisation of alkanes:synthesis,molecular structure and catalytic implications of anionic vanadium(V)oxo and peroxo complexes containing bidentate N,O ligands.J.Chem.Soc.Dalton Trans.1999,18,3169-3175.
(12)Maurya,M.R.;Agarwal,S.;Abid,M.;Azam,A.;Bader,C.;Ebel,M.;Rehder,D.Synthesis,characterisation,reactivity and in vitro antiamoebic activity of hydrazone based oxovanadium(IV),oxovanadium(V)andμ-bis(oxo)bis{oxovanadium(V)}complexes.Dalton Trans.2006,7,937-947.
(13)Zhao,W.;Yang,C.;Cheng,Z.;Zhang,Z.A reusable catalytic system for sulfide oxidation and epoxidation of allylic alcohols in water catalyzed by poly(dimethyl diallyl)ammonium/polyoxometalate.Green Chem.2016,18,995-998.
(14)Li,Z.;Schweitzer,N.M.;League,A.B.;Bernales,V.;Peters,A.W.;Getsoian,A.B.;Wang,T.C.;Miller,J.T.;Vjunov,A.;Fulton,J.L.;Lercher,J.A.;Cramer,C.J.;Gagliardi,L.;Hupp,J.T.;Farha,O.K.Sintering-resistant single-site nickel catalyst supported by metal–organic framework.J.Am.Chem.Soc.2016,138,1977-1982.
(15)Fernández,I.;Khiar,N.Recent developments in the synthesis and utilization of chiral sulfoxides.Chem.Rev.2003,103,3651-3705.
(16)Amini,M.;Naslhajian,H.;Morteza,S.;Farnia,F.;Ho?yńska,M.Selective oxidation of sulfides catalyzed by the nanocluster polyoxomolybdate(NH4)12[Mo36(NO)4O108(H2O)16].Eur.J.Inorg.Chem.2015,23,3873-3878.
(17)Salgaonkar,P.D.;Shukla,V.G.;Akamanchi,K.G.Iodic acid(HIO3)in combination with tetraethylammonium bromide as a catalyst for selective and accelerated sulfoxidation.Synth.Commun.2005,35,2805-2810.
(18)Kamata,K.;Yonehara,K.;Sumida,Y.;Yamaguchi,K.;Hikichi,S.;Mizuno,N.Efficient epoxidation of olefins with≥99%selectivity and use of hydrogen peroxide.Science 2003,300,964-966.
(19)Yadav,M.;Bhunia,A.;Jana,S.K.;Roesky,P.W.Manganese-and lanthanide-based 1D chiral coordination polymers as an enantioselective catalyst for sulfoxidation.Inorg.Chem.2016,55,2701-2708.
(20)Nikoorazm,M.;Ghorbani-Choghamarani,A.;Noori,N.Oxo-vanadium(IV)Schiff base complex supported on modified MCM-41:a reusable and efficient catalyst for the oxidation of sulfides and oxidative S-S coupling of thiols.Appl.Organomet.Chem.2015,29,328-333.
(21)Zeng,Q.;Gao,Y.;Dong,J.;Weng,W.;Zhao,Y.Vanadium-catalyzed enantioselective oxidation of allyl sulfides.Tetrahedron:asymmetry 2011,22,717-721.