近十几年来,N-杂环卡宾的配位化学和金属有机化学发展迅速,已成为均相催化反应中研究最为广泛的配体之一.在许多过渡金属催化的有机合成反应中特别是偶联反应中,N-杂环卡宾与传统有机膦配体相比具有较高的反应性.镍价格低廉,在很多反应中有望替代贵金属钯催化剂.本文总结了镍N-杂环卡宾化合物在催化交叉偶联反应和还原偶联反应中的最新应用进展.
The chemistry of N-heterocyclic carbenes(NHCs)has grown rapidly in the past decade. NHCs are now important ligands in homogeneous catalysis that show better catalytic activities than the typical phosphines in a number of transition metal catalyzed organic transformations,especially in C-C/heteroatom bond formation reactions.Ni is a much cheaper metal and the most promising alternative to Pd,and is receiving increasing attention.In this article we summarize new developments in the catalytic applications of nickel-NHC complexes in coupling reactions that include typical cross couplings of organic halides with various organometallic reagents and reductive coupling reactions.
参考文献
[1] | Arduengo A J;Harlow R L;Kline M .[J].Journal of the American Chemical Society,1991,113:361. |
[2] | McGuinness D S;Cavell K J;Skelton B W;White A H .[J].Organometallics,1999,18:1596. |
[3] | Inamoto K;Kuroda J;Sakamoto T;Hiroya K.[J].Synthesis,2007:2853. |
[4] | Lee C C;Ke W C;Chan K T;Lai C L Hu C H Lee H M .[J].Chemistry-A European Journal,2007,13:582. |
[5] | Xi Z X;Zhang X M;Chen W Z;Fu S Z Wang D Q .[J].Organometallics,2007,26:6636. |
[6] | Chiu P L;Lai C L;Chang C F;Hu C H Lee H M .[J].Organometallics,2005,24:6169. |
[7] | Wolf J;Labande A;Daran JC;Poli R .Nickel(II) complexes with bifunctional phosphine-imidazolium ligands and their catalytic activity in the Kumada-Corriu coupling reaction[J].Journal of Organometallic Chemistry,2006(3):433-443. |
[8] | Schneider SK;Rentzsch CF;Krueger A;Raubenheimer HG;Herrmann WA .Pyridin- and quinolinylidene nickel carbene complexes as effective catalysts for the Grignard cross-coupling reaction[J].Journal of molecular catalysis, A. Chemical,2007(1/2):50-58. |
[9] | Xi Z X;Liu B;Chen W Z .[J].Journal of Organic Chemistry,2008,73:3954. |
[10] | Bohm VPW.;Gstottmayr CWK.;Herrmann WA.;Weskamp T. .Nickel-catalyzed cross-coupling of aryl chlorides with aryl Grignard reagents[J].Angewandte Chemie International Edition,2000(9):1602-160+. |
[11] | B(o)hm V P W;Gst(o)ttmayr C W K;Weskamp T;Herrmann W A .[J].Angewandte Chemie International Edition,2001,40:3387. |
[12] | Zhou YB;Xi ZX;Chen WZ;Wang DQ .Dinickel(II) Complexes of Bis(N-heterocyclic carbene) Ligands Containing [Ni-2(mu-OH)] Cores as Highly Efficient Catalysts for the Coupling of Aryl Chlorides[J].Organometallics,2008(22):5911-5920. |
[13] | Xi ZX;Zhou YB;Chen WZ .Efficient Negishi Coupling Reactions of Aryl Chlorides Catalyzed by Binuclear and Mononuclear Nickel-N-Heterocyclic Carbene Complexes[J].The Journal of Organic Chemistry,2008(21):8497-8501. |
[14] | Inamoto K;Kuroda J;Danjo T;Sakamoto T .Highly efficient nickel-catalyzed heck reaction using Ni(acac)(2)/N-heterocyclic carbene catalyst[J].Synlett,2005(10):1624-1626. |
[15] | Gradel B;Brenner E;Schneider R L;Fort Y .[J].Tetrahedron Letters,2001,42:5689. |
[16] | Sato Y;Sawaki R;Mori M .[J].Organometallics,2001,20:5510. |
[17] | Matsubara K;Ueno K;Koga Y;Hara K .[J].Journal of Organic Chemistry,2007,72:5069. |
[18] | Duong H A;Cross M J;Louie J .[J].Journal of the American Chemical Society,2004,126:11438. |
[19] | Tekavec TN;Arif AM;Louie J .Regioselectivity in nickel(0) catalyzed cycloadditions of carbon dioxide with diynes[J].Tetrahedron,2004(34):7431-7437. |
[20] | Tekevac TN;Louie J .Nickel-catalyzed cycloaddition of unsaturated hydrocarbons and carbonyl compounds[J].Organic letters,2005(18):4037-4039. |
[21] | Duong HA;Louie J .A nickel(0) catalyzed cycloaddition of alkynes and isocyanates that affords pyrimidine-diones[J].Tetrahedron,2006(32):7552-7559. |
[22] | Tekavec TN;Zuo G;Simon K;Louie J .An in situ approach for nickel-catalyzed cycloaddition[J].The Journal of Organic Chemistry,2006(15):5834-5836. |
[23] | McGuinness DS.;Mueller W.;Wasserscheid P.;Cavell KJ.;Skelton BW. White AH.;Englert U. .Nickel(II) heterocyclic carbene complexes as catalysts for olefin dimerization in an imidazolium chloroaluminate ionic liquid[J].Organometallics,2002(1):175-181. |
[24] | MacKinnon AL.;Baird MC. .The synthesis and X-ray structure of trans-NiCl2(1,3-bis (2,6-diisopropylphenyl)imidazol-2-ylidene)(2); attempts to polymerize olefins utilizing a nickel(II) complex of a sterically demanding N-heterocyclic carbene[J].Journal of Organometallic Chemistry,2003(1):114-119. |
[25] | Wang X;Liu S;Jin GX .Preparation, structure, and olefin polymerization behavior of functionalized nickel(II) N-heterocyclic carbene complexes[J].Organometallics,2004(25):6002-6007. |
[26] | Ketz B E;Ottenwaelder X G;Waymouth R M.[J].Chemical Communications,2005:5693. |
[27] | Li W F;Sun H M;Chen M Z;Wang Z G Hu D M Shen Q Zhang Y .[J].Organometallics,2005,24:5925. |
[28] | Buchowicz W;Koziol A;Jerzykiewicz L B;Lis T Pasynkiewicz S Pecherzewska A Pietrzykowski A .[J].Journal of Molecular Catalysis A:Chemical,2006,257:118. |
[29] | Benson S;Payne B;Waymouth R M .[J].Journal of POLYMER SCIENCE PART A:POLYMER CHEMISTRY,2007,45:3637. |
[30] | Li W F;Sun H M;Chen M Z;Shen Q Zhang Y .[J].J Organomet Chen,2008,693:2047. |
[31] | Sujith S;Noh EK;Lee BY;Han JW .Synthesis, characterization, and norbornene polymerization of eta(3)-benzylnickel(II) complexes of N-heterocyclic carbenes[J].Journal of Organometallic Chemistry,2008(12):2171-2176. |
[32] | Xie, LZ;Sun, HM;Hu, DM;Liu, ZH;Shen, Q;Zhang, Y .Synthesis and structure of indenylnickel(II) chlorides bearing free N-heterocyclic carbene ligands and their catalysis for styrene polymerization[J].Polyhedron: The International Journal for Inorganic and Organometallic Chemistry,2009(13):2585-2590. |
[33] | Buchowicz, W;Wojtczak, W;Pietrzykowski, A;Lupa, A;Jerzykiewicz, LB;Makal, A;Wozniak, K .Synthesis, Structure, and Polymerization Activity of Cyclopentadienylnickel(II) N-Heterocyclic Carbene Complexes: Selective Cross-Metathesis in Metal Coordination Spheres[J].European journal of inorganic chemistry,2010(4):648-656. |
[34] | Schaub T;Radius U .Efficient C-F and C-C activation by a novel N-heterocyclic carbene-nickel(0) complex[J].Chemistry: A European journal,2005(17):5024-5030. |
[35] | Kuhl S.;Schneider R.;Fort Y. .Transfer hydrogenation of imines catalyzed by a nickel(0)/NHC complex[J].Organometallics,2003(21):4184-4186. |
[36] | Desmarets C.;Kuhl S.;Schneider R.;Fort Y. .Nickel(0)/imidazolium chloride catalyzed reduction of aryl halides[J].Organometallics,2002(8):1554-1559. |
[37] | Diez-Gonzalez, S;Marion, N;Nolan, SP .N-Heterocyclic Carbenes in Late Transition Metal Catalysis[J].Chemical Reviews,2009(8):3612-3676. |
[38] | Tekavec T N;Louie J .[J].Topics in Physical Organometallic Chemistry,2007,21:159. |
[39] | Poyatos, M;Mata, JA;Peris, E .Complexes with Poly(N-heterocyclic carbene) Ligands: Structural Features and Catalytic Applications[J].Chemical Reviews,2009(8):3677-3707. |
[40] | Kremzow D;Seidel G;Lehmann C W;Furstner A .[J].Chemistry-A European Journal,2005,11:1833. |
[41] | Matsubara K;Ueno K;Shibata Y .Synthesis and structures of nickel halide complexes bearing mono- and bis-coordinated N-heterocyclic carbene ligands, catalyzing Grignard cross-coupling reactions[J].Organometallics,2006(14):3422-3427. |
[42] | Gu SJ;Chen WZ .Pincer Complexes of Palladium- and Nickel-Containing 3-Butyl-1-(1,10-phenanthrolin-2-yl)imidazolylidene as Efficient Aqueous Sonogashira and Kumada Coupling Reactions[J].Organometallics,2009(3):909-914. |
[43] | Liu, AL;Zhang, XM;Chen, WZ .New Pincer CC ' C Complexes of Nickel(II) via Chloronickelation of Alkyne-Bearing N-Heterocyclic Carbenes[J].Organometallics,2009(16):4868-4871. |
[44] | Zhang, C;Wang, ZX .N-Heterocyclic Carbene-Based Nickel Complexes: Synthesis and Catalysis in Cross-Couplings of Aryl Chlorides with ArMX (M = Mg or Zn)[J].Organometallics,2009(22):6507-6514. |
[45] | Kim, C.-B.;Jo, H.;Ahn, B.-K.;Kim, C.K.;Park, K. .Nickel N-heterocyclic carbene catalyst for cross-coupling of neopentyl arenesulfonates with methyl and primary alkyl Grignard reagents[J].The Journal of Organic Chemistry,2009(24):9566-9569. |
[46] | Huynh H V;Jothibasu R.[J].European Journal of Inorganic Chemistry,2009:1926. |
[47] | Berding, J;Lutz, M;Spek, AL;Bouwman, E .Synthesis of Novel Chelating Benzimidazole-Based Carbenes and Their Nickel(II) Complexes: Activity in the Kumada Coupling Reaction[J].Organometallics,2009(6):1845-1854. |
[48] | Berding, J;van Dijkman, TF;Lutz, M;Spek, AL;Bouwman, E .N-donor functionalized N-heterocyclic carbene nickel(II) complexes in the Kumada coupling[J].Dalton transactions: An international journal of inorganic chemistry,2009(35):6948-6955. |
[49] | Miyazaki, S;Koga, Y;Matsumoto, T;Matsubara, K .A new aspect of nickel-catalyzed Grignard cross-coupling reactions: selective synthesis, structure, and catalytic behavior of a T-shape three-coordinate nickel(I) chlorDEe bearing a bulky NHC ligand[J].Chemical communications,2010(11):1932-1934. |
[50] | Lee HM;Chiu PL;Zeng JY .A convenient synthesis of phosphine-functionalized N-heterocyclic carbene ligand precursors, structural characterization of their palladium complexes and catalytic application in Suzuki coupling reaction[J].Inorganica Chimica Acta,2004(14):4313-4321. |
[51] | Liao C Y;Chan K T;Chang Y C;Chen C Y Tu C Y Hu C H Lee H M .[J].Organometallics,2007,26:5826. |
[52] | Kuroda J I;Inamoto K;Hiroya K;Doi T.[J].European Journal of Organic Chemistry,2009:2251. |
[53] | Inamoto K;Kuroda J;Kwon E;Hiroya K;Doi T .Pincer-type bis(carbene)-derived complexes of nickel(II): Synthesis, structure, and catalytic activity[J].Journal of Organometallic Chemistry,2009(3):389-396. |
[54] | Herrmann W A;Elison M;Fischer J;K(o)cher C,Artus G R J .[J].Angewandte Chemie International Edition,1995,34:2371. |
[55] | Zhang XM;Xi ZX;Liu AL;Chen WZ .Facile and efficient olefination of aryl halides catalyzed by a palladium complex containing a heteroarene-functionalized N-heterocyclic carbene[J].Organometallics,2008(17):4401-4406. |
[56] | Zhang XM;Liu AL;Chen WZ .Pd-catalyzed efficient one-pot sequential cross-coupling reactions of aryl dihalides[J].Organic letters,2008(17):3849-3852. |
[57] | Ye JS;Chen W;Wang D .Synthesis, structural characterization, and catalytic behaviour in Heck coupling of palladium(II) complexes containing pyrimidine-functionalized N-heterocyclic carbenes[J].Dalton transactions: An international journal of inorganic chemistry,2008(30):4015-4022. |
[58] | McGuinness D S;Cavell K J .[J].Organometallics,2000,19:741. |
[59] | Grundemann S;Albrecht M;Loch J A;Faller J W Crabtree R H.[J].Organometallics,2001:205485. |
[60] | Peris E;Loch J A;Mata J;Crabtree R H.[J].Chemical Communications,2001:201. |
[61] | Loch JA.;Albrecht M.;Peris E.;Mata J.;Faller JW.;Crabtree RH. .Palladium complexes with tridentate pincer bis-carbene Ligands as efficient catalysts for C-C coupling[J].Organometallics,2002(4):700-706. |
[62] | Inamoto K;Kuroda J;Hiroya K;Noda Y;Watanabe M;Sakamoto T .Synthesis and catalytic activity of a pincer-type bis(imidazolin-2-ylidene) nickel(II) complex[J].Organometallics,2006(12):3095-3098. |
[63] | Manolikakes G;Dastbaravardeh N;Knochel P .Nickel-catalyzed cross-coupling reactions of Aryltitanium(IV) alkoxides with aryl halides[J].Synlett,2007(13):2077-2080. |
[64] | Leleu A;Fort Y;Schneider R .Nickel(0)/imidazolium carbene catalyst system for efficient cross-coupling of aryl bromides and chlorides with organomanganese reagents[J].Advanced synthesis & catalysis,2006(9):1086-1092. |
[65] | Viciu M S;Kissling R M;Stevens E D;Nolan S P .[J].Organic Letters,2002,4:2229. |
[66] | Stauffer S R;Lee S;Stambuli J P;Hauck S I Hartwig J F .[J].Organic Letters,2000,2:1423. |
[67] | Desmarets C.;Schneider R.;Fort Y. .Nickel (0)/dihydroimidazol-2-ylidene complex catalyzed coupling of aryl chlorides and amines[J].The Journal of Organic Chemistry,2002(9):3029-3036. |
[68] | Kuhl S;Fort Y;Schneider R .Nickel(0)/N-heterocyclic carbene complexes catalysed arylation of aromatic diamines[J].Journal of Organometallic Chemistry,2005(24/25):6169-6177. |
[69] | Omar-Amrani R;Thomas A;Brenner E;Schneider R Fort Y .[J].Organic Letters,2003,5:2311. |
[70] | Kelly RA;Scott NM;Diez-Gonzalez S;Stevens ED;Nolan SP .Simple synthesis of CpNi(NHC)Cl complexes (Cp = cyclopentadienyl; NHC=N-heterocyclic carbene)[J].Organometallics,2005(14):3442-3447. |
[71] | Chen C;Yang L M .[J].Journal of Organic Chemistry,2007,72:6324. |
[72] | Gao CY;Yang LM .Nickel-catalyzed amination of aryl tosylates[J].The Journal of Organic Chemistry,2008(4):1624-1627. |
[73] | Matsubara K;Miyazaki S;Koga Y;Nibu Y;Hashimura T;Matsumoto T .An Unsaturated Nickel(0) NHC Catalyst: Facile Preparation and Structure of Ni(0)(NHC)(2), Featuring a Reduction Process from Ni(II)(NHC)(acac)(2)[J].Organometallics,2008(22):6020-6024. |
[74] | Tobisu M;Shimasaki T;Chatani N .[J].Chemistry Letters,2009,38:710. |
[75] | Shimasaki T;Tobisu M;Chatani N .[J].Angewandte Chemie International Edition,2010,49:2929. |
[76] | Zhang YG;Ngeow KC;Ying JY .The first n-heterocyclic carbene-based nickel catalyst for C-S coupling[J].Organic letters,2007(18):3495-3498. |
[77] | Huynh HV;Wong LR;Ng PS .Anagostic interactions and catalytic activities of sterically bulky benzannulated N-heterocyclic carbene complexes of nickel(II)[J].Organometallics,2008(10):2231-2237. |
[78] | Ding N;Zhang J;Hor TSA .Formation and crystallographic elucidation of stable [4+2]-coordinate nickel(II) N,S-heterocyclic carbene (NSHC) complexes[J].Dalton transactions: An international journal of inorganic chemistry,2009(10):1853-1858. |
[79] | Ng S-S;Jamison T F .[J].Journal of the American Chemical Society,2005,127:7320. |
[80] | Sawaki R;Sato Y;Mori M .[J].Organic Letters,2004,6:1131. |
[81] | Mahandru G M;Liu G;Montgomery J .[J].Journal of the American Chemical Society,2004,126:3698. |
[82] | Knapp-Reed B;Mahandru G M;Montgomery J .[J].Journal of the American Chemical Society,2005,127:13156. |
[83] | Chaulagain M R;Sormunen G J;Montgomery J .[J].Journal of the American Chemical Society,2007,129:9568. |
[84] | Sato Y;Hinata Y;Seki R;Oonishi Y Saito N .[J].Organic Letters,2007,9:5597. |
[85] | Malik, HA;Chaulagain, MR;Montgomery, J .Cooperativity of Regiochemistry Control Strategies in Reductive Couplings of Propargyl Alcohols and Aldehydes[J].Organic letters,2009(24):5734-5737. |
[86] | Malik, H.A.;Sormunen, G.J.;Montgomery, J. .A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes[J].Journal of the American Chemical Society,2010(18):6304-6305. |
[87] | Murakami M;Ashida S;Matsuda T .[J].Journal of the American Chemical Society,2005,127:6932. |
[88] | Herath A;Li W;Montgomery J .[J].Journal of the American Chemical Society,2007,130:469. |
- 下载量()
- 访问量()
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%