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第6期 金金等: Grubbs催化剂合成研究进展 575 heterocyclic carbene ruthenium pre)catalysts [J] cylic carbene-containing metal complexes from 2-( Pen- CataL. Sci. Technol.. 2011. 1. 1287-1297 tafluorophenyl )imidazolidines [J]. Organometallics [37] Weskamp T, Schattermann W C, Spiegler M, et aL.A 2007,26(8):2122-2124 novel class of ruthenium catalysts for olefin metathesis [46 Voutchkova A M, Appelhans L N, Crabtree R H, et al []. anger.Chem.lnt.Ed.,1998,37(18):2490 Disubstituted imidazolium-2-carboxylates as efficient pre- cursors to N-heterocyclic carbene complexes of Rh, Ru [38 Arduengo Ill A J, Krafezyk R, Schmutzler R. Imid- Ir, and Pd [J.J. Am. Chem. Soc., 2005, 127(50) olylidenes, imidazolinylidenes and imidazolidines [J] 17624-17625 Tetrahedron,1999,55(51):14523-14534 [47] Voutchkova A M, Feliz M, Crabtree R H, et al. Imidazo- [39] Viciu M S, Grasa G A, Nolan S P. Catalytic dehalogena- lium carboxylates as versatile and selective N-heterocyclic tion of aryl halides mediated by a palladium/imidazolium arene transfer agents: synthesis, mechanism and appl salt system [J]. Organometallics, 2001, 20( 16) cations [J]. J. Am. Chem. Soc., 2007, 129(42) 12834-12846 [40] Jafarpour L, Hillier A C, Nolan S P. Improved one-pot [48] Sauvage X, Demonceau A, Delaude L. Imidazol in) sis catalysts [J]. Organometallics, 2002, 21(2):442 for the synthesis of second generation ruthenium metate- sis catalysts [J]. Ade. Synth. CataL., 2009, 351(11/ [41] Jafarpour L, Nolan S P. Simple and convenient synthetic 2):2031-2038 procedure leading to ruthenium olefin metathesis catalysts [49] Tudose A, Demonceau A, Delaude L Imidazol( in)ium bearing the N, N-Bis( mesityl imidazol-2-ylidene rboxylates as N-heterocyclic carbene precursors in ru- IMes) ligand [J]. Organometallics, 2000, 19(11) propanation [J].J. Organomet. Chem.,2006,691 [42] Trmka T M, Morgan J P, Grubbs R H. Synthesis and ac- (24/25):5356-5365 tivity of ruthenium alkylidene complexes coordinated with [50 Kingsbury J S, Harrity J P A, Hoveyda A H, et al. A re- hosphine and N-heterocyclic carbene ligands [J]. J. yclable Ru-based metathesis catalyst [J]. J.Am 4m.Chem.Soc.,2003,125(9):2546-2558 Chem.Soe.,1999,121(4):791-799 [43 Arduengo Ill A J, Calabrese J C, Davidson F, et al. [51 Hoveyda A H, Gillingham D G, Veldhuizen JJ V, et al. C-H insertion reactions of nucleophilic carbenes [J] exes bearing bidentate carbenes: from innocent Helt.Chim.Acta.,1999,82(12):2348-2364 uriosity to uniquely effective catalysts for olefin metate- [44 Nyce G W, Csihony S, Waymouth R M, et aL. A general [J]. Org. BiomoL. Chem., 2004, 2:8-23 and versatile approach to thermally generated N-heterocy. [52] Gessler S, Randl S, Blechert S. Synthesis and metathe- clic carbenes [J]. Chem. Eur. J., 2004, 10( 16) reactions of a phosphine-free dihydroimidazole ca 4073-4079 lex []. Tetrahedron Lett.,2000, 4 [45]Blum A P, Ritter T, Grubbs R H. Synthesis of N-hetero-heterocycliccarbeneruthenium (pre)catalysts[J]. Catal.Sci.Technol.,2011,1:1287-1297 [37] WeskampT,SchattermannW C,SpieglerM,etal.A novelclassofruthenium catalystsforolefinmetathesis [J].Angew.Chem.Int.Ed.,1998,37(18):2490- 2493 [38] ArduengoIIIA J,KrafczykR,SchmutzlerR.Imid azolylidenes,imidazolinylidenesandimidazolidines[J]. Tetrahedron,1999,55(51):14523-14534 [39] ViciuMS,GrasaGA,NolanSP.Catalyticdehalogena tionofarylhalidesmediatedbyapalladium/imidazolium saltsystem [J].Organometallics,2001,20(16): 3607-3612 [40] JafarpourL,HillierAC,NolanSP.Improvedonepot synthesisofsecondgenerationrutheniumolefinmetathe siscatalysts[J].Organometallics,2002,21(2):442- 444 [41] JafarpourL,NolanSP.Simpleandconvenientsynthetic procedureleadingtorutheniumolefinmetathesiscatalysts bearingthe N,N’Bis(mesityl)imidazol2ylidene (IMes)ligand[J].Organometallics,2000,19(11): 2055-2057 [42] TrnkaTM,MorganJP,GrubbsRH.Synthesisandac tivityofrutheniumalkylidenecomplexescoordinatedwith phosphineandNheterocycliccarbeneligands[J].J. Am.Chem.Soc.,2003,125(9):2546-2558 [43] ArduengoIIIAJ,CalabreseJC,DavidsonF,etal. C—Hinsertionreactionsofnucleophiliccarbenes[J]. Helv.Chim.Acta.,1999,82(12):2348-2364 [44] NyceGW,CsihonyS,WaymouthRM,etal.Ageneral andversatileapproachtothermallygeneratedNheterocy cliccarbenes[J].Chem.Eur.J.,2004,10(16): 4073-4079 [45] BlumAP,RitterT,GrubbsRH.SynthesisofNhetero cyliccarbenecontainingmetalcomplexesfrom2(Pen tafluorophenyl)imidazolidines[J]. Organometallics, 2007,26(8):2122-2124 [46] VoutchkovaAM,AppelhansLN,CrabtreeRH,etal. Disubstitutedimidazolium2carboxylatesasefficientpre cursorstoNheterocycliccarbenecomplexesofRh,Ru, Ir,andPd[J].J.Am.Chem.Soc.,2005,127(50): 17624-17625 [47] VoutchkovaAM,FelizM,CrabtreeRH,etal.Imidazo liumcarboxylatesasversatileandselectiveNheterocyclic carbenetransferagents:synthesis,mechanismandappli cations[J].J.Am.Chem.Soc.,2007,129(42): 12834-12846 [48] SauvageX,DemonceauA,DelaudeL.Imidazol(in) ium2carboxylatesasNheterocycliccarbeneprecursors forthesynthesisofsecondgenerationrutheniummetathe siscatalysts[J].Adv.Synth.Catal.,2009,351(11/ 12):2031-2038 [49] TudoseA,DemonceauA,DelaudeL.Imidazol(in)ium 2carboxylatesasNheterocycliccarbeneprecursorsinru thenium! arenecatalystsforolefinmetathesisandcyclo propanation[J].J.Organomet.Chem.,2006,691 (24/25):5356-5365 [50] KingsburyJS,HarrityJPA,HoveydaAH,etal.Are cyclableRubasedmetathesiscatalyst[J].J.Am. Chem.Soc.,1999,121(4):791-799 [51] HoveydaAH,GillinghamDG,VeldhuizenJJV,etal. Rucomplexesbearingbidentatecarbenes:frominnocent curiositytouniquelyeffectivecatalystsforolefinmetathe sis[J].Org.Biomol.Chem.,2004,2:8-23 [52] GesslerS,RandlS,BlechertS.Synthesisandmetathe sisreactionsofaphosphinefreedihydroimidazolecarbene rutheniumcomplex[J].TetrahedronLett.,2000,41: 9973-9976 第 6期 胡金金等:Grubbs催化剂合成研究进展 575
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