过渡金属催化的烯烃异构反应在有机化合物合成、日用化学品合成、原料油应用和天然产物合成中都有着举足轻重的作用.廉价过渡金属由于其在资源、价格、后处理等方面的优势,日益受到研究者的重视.本文主要综述了近几十年来廉价过渡金属铁、钴、镍在催化烯烃异构反应方面的研究进展,详细阐述了不同的催化体系在催化活性、反应选择性、底物适用性及反应机理方面的特点.虽然目前的催化体系已经表现出优异的性能与应用价值,但在烯烃异构的立体选择性、区域选择性机制等方面,仍然需要更深入的研究.
参考文献
| [1] | Sakthivel, Ayyamperumal;Mahato, Nihar Ranjan;Baskaran, Thangaraj;Christopher, Jayaraj.Molybdenum carbonyl grafted onto silicate intercalated cobalt-aluminum hydrotalcite: A new potential catalyst for the hydroformylation of octene[J].Catalysis Communications,2015:55-61. |
| [2] | Mei Xue;Jiayun Li;Jiajian Peng.Effect of triarylphosphane ligands on the rhodium-catalyzed hydrosilylation of alkene[J].Applied Organometallic Chemistry,20142(2):120-126. |
| [3] | Komine, Nobuyuki;Abe, Makoto;Suda, Ryoko;Hirano, Masafumi.Markovnikov-Selective Hydrosilylation of Electron-Deficient Alkenes with Arylsilanes Catalyzed by Mono(phosphine)palladium(0)[J].Organometallics,20152(2):432-437. |
| [4] | Lee, W.-C.;Wang, C.-H.;Lin, Y.-H.;Shih, W.-C.;Ong, T.-G..Tandem isomerization and C-H activation: Regioselective hydroheteroarylation of allylarenes[J].Organic letters,201320(20):5358-5361. |
| [5] | Huang YH;Dass RI;Xing ZL;Goodenough JB.Double perovskites as anode materials for solid-oxide fuel cells.[J].Science,20065771(5771):254-257. |
| [6] | Biswas, S.;Huang, Z.;Choliy, Y.;Wang, D.Y.;Brookhart, M.;Krogh-Jespersen, K.;Goldman, A.S..Olefin isomerization by iridium pincer catalysts. experimental evidence for an η ~3-allyl pathway and an unconventional mechanism predicted by DFT calculations[J].Journal of the American Chemical Society,201232(32):13276-13295. |
| [7] | WU Qiang;JIN Rizhe;KANG Chuanqing;CHEN Wenhui;BIAN Zheng;MA Xiaoye;DING Jinying.Ni-Catalyzed Cross Coupling of Aryl Grignard Reagents with Aryl Halides in a Nonpolar Solvent and an Efficient Synthesis of Biaryls Under Neat Conditions[J].高等学校化学研究（英文版）,2016(1):55-61. |
| [8] | Fu-She Han.Transition-metal-catalyzed Suzuki-Miyaura cross-coupling reactions: a remarkable advance from palladium to nickel catalysts[J].Chemical Society Reviews,201312(12):5270-5298. |
| [9] | Hwan Jung Lim;Craig R. Smith;T. V. RajanBabu.Facile Pd(II)- and Ni(II)-Catalyzed Isomerization of Terminal Alkenes into 2-Alkenes[J].The Journal of Organic Chemistry,200912(12):4565-4572. |
| [10] | Gauthier, D.;Lindhardt, A.T.;Olsen, E.P.K.;Overgaard, J.;Skrydstrup, T..In situ generated bulky palladium hydride complexes as catalysts for the efficient isomerization of olefins. Selective transformation of terminal alkenes to 2-alkenes[J].Journal of the American Chemical Society,201023(23):7998-8009. |
| [11] | Franqe-Aimee Alphonse;Andrei K.Yudin.Rhodium-Catalyzed Stereoselective Formation of Z-Enamines from Allylaziridines[J].Journal of the American Chemical Society,200636(36):11754-11755. |
| [12] | Tsang DS;Yang S;Alphonse FA;Yudin AK.Stereoselective isomerisation of N-allyl aziridines into geometrically stable Z enamines by using rhodium hydride catalysis[J].Chemistry: A European journal,20083(3):886-894. |
| [13] | Zhuo, L.-G.;Yao, Z.-K.;Yu, Z.-X..Synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones[J].Organic letters,201318(18):4634-4637. |
| [14] | Arisawa M;Terada Y;Takahashi K;Nakagawa M;Nishida A.Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles[J].The Journal of Organic Chemistry,200611(11):4255-4261. |
| [15] | Hanessian S;Giroux S;Larsson A.Efficient allyl to propenyl isomerization in functionally diverse compounds with a thermally modified grubbs second-generation catalyst[J].Organic letters,200624(24):5481-5484. |
| [16] | Sumeet K.Sharma;Vivek K.Srivastava;Raksh V.Jasra.Selective double bond isomerization of allyl phenyl ethers catalyzed by ruthenium metal complexes[J].Journal of molecular catalysis, A. Chemical,20061/2(1/2):200-209. |
| [17] | Douglas B. Grotjahn;Casey R. Larsen;Jeffery L. Gustafson.Extensive Isomerization of Alkenes Using a Bifunctional Catalyst: An Alkene Zipper[J].Journal of the American Chemical Society,200731(31):9592-9593. |
| [18] | Larsen, C.R.;Grotjahn, D.B..Stereoselective alkene isomerization over one position[J].Journal of the American Chemical Society,201225(25):10357-10360. |
| [19] | Casey R. Larsen;Gulin Erdogan;Douglas B. Grotjahn.General Catalyst Control of the Monoisomerization of 1?Alkenes to trans-2-Alkenes[J].Journal of the American Chemical Society,20144(4):1226-1229. |
| [20] | Chianese, A.R.;Shaner, S.E.;Tendler, J.A.;Pudalov, D.M.;Shopov, D.Y.;Kim, D.;Rogers, S.L.;Mo, A..Iridium complexes of bulky CCC-pincer N-heterocyclic carbene ligands: Steric control of coordination number and catalytic alkene isomerization[J].Organometallics,201221(21):7359-7367. |
| [21] | Spring Melody M. Knapp;Sarah E. Shaner;Daniel Kim;Dimitar Y. Shopov;Jennifer A. Tendler;David M. Pudalov;Anthony R. Chianese.Mechanistic Studies of Alkene Isomerization Catalyzed by CCCPincer Complexes of Iridium[J].Organometallics,20142(2):473-484. |
| [22] | Yamamoto, Yasunori;Miyairi, Takahiro;Ohmura, Toshimichi;Miyaura, Norio.Synthesis of chiral esters of (E)-3-(silyloxy)-2-propenylboronic acid via the iridium-catalyzed isomerization of the double bond[J].The Journal of Organic Chemistry,19991(1):296-0. |
| [23] | Sivaramakrishna A;Mushonga P;Rogers IL;Zheng F;Haines RJ;Nordlander E;Moss JR.Selective isomerization of 1-alkenes by binary metal carbonyl compounds[J].Polyhedron: The International Journal for Inorganic and Organometallic Chemistry,20087(7):1911-1916. |
| [24] | Inigo Gottker-Schnetmann;Peter White;Maurice Brookhart.Iridium Bis(phosphinite) p-XPCP Pincer Complexes: Highly Active Catalysts for the Transfer Dehydrogenation of Alkanes[J].Journal of the American Chemical Society,20046(6):1804-1811. |
| [25] | Chi Chen;Thomas R. Dugan;William W. Brennessel;Daniel J. Weix;Patrick L. Holland.Z?Selective Alkene Isomerization by High-Spin Cobalt(II) Complexes[J].Journal of the American Chemical Society,20143(3):945-955. |
| [26] | Courchay FC;Sworen JC;Ghiviriga I;Abboud KA;Wagener KB.Understanding structural isomerization during ruthenium-catalyzed olefin metathesis: A deuterium labeling study[J].Organometallics,200626(26):6074-6086. |
| [27] | Morrill TC.;D'Souza CA..Efficient hydride-assisted isomerization of alkenes via rhodium catalysis[J].Organometallics,20038(8):1626-1629. |
| [28] | Larionov, Evgeny;Lin, Luqing;Guenee, Laure;Mazet, Clement.Scope and Mechanism in Palladium-Catalyzed Isomerizations of Highly Substituted Allylic, Homoallylic, and Alkenyl Alcohols[J].Journal of the American Chemical Society,201448(48):16882-16894. |
| [29] | Arkaitz Correa;Olga Garcia Mancheno;Carsten Bolm.Iron-catalysed carbon-heteroatom and heteroatom-heteroatom bond forming processes[J].Chemical Society Reviews,20086(6):1108-1117. |
| [30] | Bauer Eike B.Recent Advances in Iron Catalysis in Organic Synthesis[J].Current organic chemistry,200816(16):1341-1369. |
| [31] | Reddy MR.;Periasamy M..ISOMERIZATION OF 1-ALKENES USING THE NA2FE(CO)(4)/CUCL AND NA2FE(CO)(4)/BRCH2CH2BR REAGENT SYSTEMS[J].Journal of Organometallic Chemistry,19951/2(1/2):263-266. |
| [32] | Crivello JV.;Kong SQ..Efficient isomerization of allyl ethers and related compounds using pentacarbonyliron[J].The Journal of Organic Chemistry,199819(19):6745-6748. |
| [33] | Kobayashi T;Ohmiya H;Yorimitsu H;Oshima K.Cobalt-catalyzed regioselective dehydrohalogenation of alkyl halides with dimethylphenylsilylmethylmagnesium chloride[J].Journal of the American Chemical Society,200834(34):11276-11277. |
| [34] | Tsuneyuki Kobayashi;Hideki Yorimitsu;Koichiro Oshima.Cobalt-Catalyzed Isomerization of 1-Alkenes to (E)-2-Alkenes with Dimethylphenylsilylmethylmagnesium Chloride and Its Application to the Stereoselective Synthesis of (E)-Alkenylsilanes[J].Chemistry, an Asian journal,20097(7):1078-1083. |
| [35] | Crossley, Steven W. M.;Barabe, Francis;Shenvi, Ryan A..Simple, Chemoselective, Catalytic Olefin Isomerization[J].Journal of the American Chemical Society,201448(48):16788-16791. |
| [36] | Bricout H.;Monflier E.;Mortreux A..Isomerization of olefins in a two-phase system by homogeneous water-soluble nickel complexes[J].Journal of Organometallic Chemistry,19981/2(1/2):469-471. |
| [37] | Wille A.;Frauenrath H.;Tomm S..A highly Z-selective isomerization (double-bond migration) procedure for allyl acetals and allyl ethers mediated by nickel complexes[J].Synthesis: International Journal of Methods in Synthetic Organic Chemistry,19983(3):305-308. |
| [38] | Wang, L.;Liu, C.;Bai, R.;Pan, Y.;Lei, A..Easy access to enamides: A mild nickel-catalysed alkene isomerization of allylamides[J].Chemical communications,201372(72):7923-7925. |
| [39] | Weber, Felicia;Schmidt, Anastasia;Roese, Philipp;Fischer, Michel;Burghaus, Olaf;Hilt, Gerhard.Double-Bond Isomerization: Highly Reactive Nickel Catalyst Applied in the Synthesis of the Pheromone (9Z,12Z)-Tetradeca-9,12-dienyl Acetate[J].Organic letters,201512(12):2952-2955. |
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