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Cationic [2,6-Bis(2‘-oxazolinyl)phenyl]palladium(II) Complexes:  Catalysts for the Asymmetric Michael Reaction

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Department of Chemistry, Cardiff University, P.O. Box 912, Cardiff CF10 3TB, U.K.
Cite this: Organometallics 2000, 19, 7, 1282–1291
Publication Date (Web):March 4, 2000
https://doi.org/10.1021/om990710h
Copyright © 2000 American Chemical Society

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    Abstract

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    Reaction of 1,3-dicyanobenzene with β-amino alcohols (S)-H2NCHRCH2OH (R = iPr, iBu, tBu, CH2Cy, CH2Ph) and (R)-H2NCHPhCH2OH gave new 1,3-bis(2‘-oxazolinyl)benzenes (30−51%). These, together with 1,3-bis(4‘,4‘-dimethyl-2‘-oxazolinyl)benzene, were treated with LDA/TMEDA followed by the addition of PdBr2(1,5-COD) to give [2,6-bis(2‘-oxazolinyl)phenyl]palladium(II) bromide complexes (21−41%). In two cases no complexes were obtained (R = Ph, CH2Ph) due to ring opening of the oxazolines by LDA/TMEDA. Treatment of the palladium complexes with AgBF4, AgOTf, or AgSbF6 in wet CH2Cl2 provided a series of cationic [2,6-bis(2‘-oxazolinyl)phenyl]palladium complexes (28−87%) containing water coordinated to palladium, as established by an X-ray crystal structure analysis of (S,S)-[2,6-bis(4‘-isopropyl-2‘-oxazolinyl)phenyl]aquopalladium(II) trifluoromethanesulfonate. All of the cationic complexes proved to be efficient catalysts for the Michael reaction between α-cyanocarboxylates and methyl vinyl ketone and between acrylonitrile and activated Michael donors. Selectivities of up to 34% ee were obtained for the formation of (R)-ethyl 2-cyano-2-methyl-5-oxohexanoate.

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    Text giving full characterization data for 16a2, 16a3, 16b1, 13g, 14g, 18, and 12 and details of the X-ray structure determination of 16b2. This material is available free of charge via the Internet at http://pubs.acs.org.

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    46. Varsha Rani, Harkesh B. Singh, Ray J. Butcher. Protic and substituted NCN palladium(II) pincer complexes with 1,3-bis(benzimidazol-2′-yl)-2-bromobenzenes: Structure and catalysis. Journal of Organometallic Chemistry 2018, 859 , 33-43. https://doi.org/10.1016/j.jorganchem.2018.01.027
    47. Gavin Roffe, Sarote Boonseng, Hazel Cox, John Spencer. Unsymmetrical Pincer Palladacycles Synthesis and Reactivity. 2018, 451-466. https://doi.org/10.1016/B978-0-12-812931-9.00022-0
    48. Yasuhiro Uozumi, Go Hamasaka. Ligand-Introduction Synthesis of NCN-Pincer Complexes and their Chemical Properties. 2018, 643-672. https://doi.org/10.1016/B978-0-12-812931-9.00030-X
    49. Hugo Valdés, Juan M. Germán-Acacio, David Morales-Morales. Strategies for the design and synthesis of pincer-based dendrimers. 2018, 245-291. https://doi.org/10.1016/B978-0-12-813663-8.00007-5
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    51. Arjun Kumbhar. Functionalized nitrogen ligands for palladium catalyzed cross-coupling reactions (part I). Journal of Organometallic Chemistry 2017, 848 , 22-88. https://doi.org/10.1016/j.jorganchem.2017.07.009
    52. Katerina M. Korch, Steven A. Loskot, Brian M. Stoltz. Asymmetric Synthesis of Quaternary Stereocenters via Metal Enolates. 2017, 1-85. https://doi.org/10.1002/9780470682531.pat0858
    53. Hanumanprasad Pandiri, Vineeta Soni, Rajesh G. Gonnade, Benudhar Punji. Development of (quinolinyl)amido-based pincer palladium complexes: a robust and phosphine-free catalyst system for C–H arylation of benzothiazoles. New Journal of Chemistry 2017, 41 (9) , 3543-3554. https://doi.org/10.1039/C7NJ00452D
    54. Iwao Omae. Applications of Cyclometalation Five-Membered Ring Products and Intermediates as Catalytic Agents. Modern Research in Catalysis 2016, 05 (03) , 51-74. https://doi.org/10.4236/mrc.2016.53006
    55. Svenja Werkmeister, Jacob Neumann, Kathrin Junge, Matthias Beller. Pincer‐Type Complexes for Catalytic (De)Hydrogenation and Transfer (De)Hydrogenation Reactions: Recent Progress. Chemistry – A European Journal 2015, 21 (35) , 12226-12250. https://doi.org/10.1002/chem.201500937
    56. Takayoshi Arai, Takuma Moribatake, Hyuma Masu. Chiral Bis(imidazolidine)‐Derived NCN Pincer Rh Complex for Catalytic Asymmetric Mannich Reaction of Malononitrile with N ‐Boc Imines. Chemistry – A European Journal 2015, 21 (30) , 10671-10675. https://doi.org/10.1002/chem.201502097
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    58. María D. Díaz‐de‐Villegas, José A. Gálvez, Ramón Badorrey, Pilar López‐Ram‐de‐Víu. Organocatalysis in Enantioselective α‐Functionalization of 2‐Cyanoacetates. Advanced Synthesis & Catalysis 2014, 356 (16) , 3261-3288. https://doi.org/10.1002/adsc.201400404
    59. Kálmán J. Szabó. C–C, C–O, and C–B Bond Formation by Pincer Complexes Including Asymmetric Catalysis. 2014, 95-116. https://doi.org/10.1002/9783527681303.ch4
    60. Gerard C. Dickmu, Lothar Stahl, Irina P. Smoliakova. A new enantiopure d-camphor-derived palladacycle. Journal of Organometallic Chemistry 2014, 756 , 27-33. https://doi.org/10.1016/j.jorganchem.2014.01.011
    61. Iwao Omae. Applications of Five-Membered Ring Products as Catalysts in Cyclometalation Reactions. 2014, 139-179. https://doi.org/10.1007/978-4-431-54604-7_8
    62. W.-Q. Chen, J.-A. Ma. 4.01 Stabilized Nucleophiles with Electron Deficient Alkenes, Alkynes, Allenes. 2014, 1-85. https://doi.org/10.1016/B978-0-08-097742-3.00401-8
    63. M. Mauduit, O. Baslé, H. Clavier, C. Crévisy, A. Denicourt-Nowicki. 4.04 Metal-Catalyzed Asymmetric Nucleophilic Addition to Electron-Deficient Alkenes. 2014, 189-341. https://doi.org/10.1016/B978-0-08-097742-3.00406-7
    64. Lapo Luconi, Andrea Rossin, Alessandro Motta, Giulia Tuci, Giuliano Giambastiani. Group IV Organometallic Compounds Based on Dianionic “Pincer” Ligands: Synthesis, Characterization, and Catalytic Activity in Intramolecular Hydroamination Reactions. Chemistry – A European Journal 2013, 19 (15) , 4906-4921. https://doi.org/10.1002/chem.201203644
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    66. Gemma R. Freeman, J. A. Gareth Williams. Metal Complexes of Pincer Ligands: Excited States, Photochemistry, and Luminescence. 2013, 89-129. https://doi.org/10.1007/978-3-642-31081-2_4
    67. Kálmán J. Szabó. Pincer Complexes as Catalysts in Organic Chemistry. 2013, 203-241. https://doi.org/10.1007/978-3-642-31081-2_7
    68. Jun-ichi Ito, Hisao Nishiyama. Optically Active Bis(oxazolinyl)phenyl Metal Complexes as Multipotent Catalysts. 2013, 243-270. https://doi.org/10.1007/978-3-642-31081-2_8
    69. Simon H. Eitel, Sascha Jautze, Wolfgang Frey, René Peters. Asymmetric Michael additions of α-cyanoacetates by soft Lewis acid/hard Brønsted acid catalysis: stereodivergency with bi- vs. monometallic catalysts. Chemical Science 2013, 4 (5) , 2218. https://doi.org/10.1039/c3sc50419k
    70. Jun-ichi Ito, Hisao Nishiyama. Asymmetric Catalysis Mediated by Optically Active Bis(oxazolinyl)phenyl Metal Complexes. Journal of Synthetic Organic Chemistry, Japan 2013, 71 (8) , 791-803. https://doi.org/10.5059/yukigoseikyokaishi.71.791
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    72. K. Tomioka, Y. Yamamoto, K.-i Yamada. 4.7 C–C Bond Formation (Transition Metal-Catalyzed Michael). 2012, 122-131. https://doi.org/10.1016/B978-0-08-095167-6.00406-7
    73. Kengo Hyodo, Shuichi Nakamura, Kotaro Tsuji, Takahiro Ogawa, Yasuhiro Funahashi, Norio Shibata. Enantioselective Reaction of Imines and Benzyl Nitriles Using Palladium Pincer Complexes with C 2 ‐Symmetric Chiral Bis(imidazoline)s. Advanced Synthesis & Catalysis 2011, 353 (18) , 3385-3390. https://doi.org/10.1002/adsc.201100626
    74. Kenneth J.H. Young, Xianhui Bu, William C. Kaska. Synthesis, characterization, and cyclometalation studies of benzo[1,2-h: 5,4-h′]diquinolines with palladium and platinum. Journal of Organometallic Chemistry 2011, 696 (25) , 3992-3997. https://doi.org/10.1016/j.jorganchem.2011.08.012
    75. Sharad Kumar Panday. Advances in the chemistry of proline and its derivatives: an excellent amino acid with versatile applications in asymmetric synthesis. Tetrahedron: Asymmetry 2011, 22 (20-22) , 1817-1847. https://doi.org/10.1016/j.tetasy.2011.09.013
    76. Jaya Prakash Das, Ilan Marek. Enantioselective synthesis of all-carbon quaternary stereogenic centers in acyclic systems. Chemical Communications 2011, 47 (16) , 4593. https://doi.org/10.1039/c0cc05222a
    77. Qun-Li Luo, Jian-Ping Tan, Zhi-Fu Li, Yue Qin, Lin Ma, Dong-Rong Xiao. Novel bis(azole) pincer palladium complexes: synthesis, structures and applications in Mizoroki–Heck reactions. Dalton Transactions 2011, 40 (14) , 3601. https://doi.org/10.1039/c0dt01414a
    78. Dan-Dan Shao, Jun-Long Niu, Xin-Qi Hao, Jun-Fang Gong, Mao-Ping Song. Neutral and cationic chiral NCN pincer nickel(ii) complexes with 1,3-bis(2′-imidazolinyl)benzenes: synthesis and characterization. Dalton Transactions 2011, 40 (35) , 9012. https://doi.org/10.1039/c1dt10329f
    79. Gang Xu, Qunli Luo, Stefan Eibauer, Andreas F. Rausch, Sabine Stempfhuber, Manfred Zabel, Hartmut Yersin, Oliver Reiser. Palladium(ii)- and platinum(ii)phenyl-2,6-bis(oxazole) pincer complexes: Syntheses, crystal structures, and photophysical properties. Dalton Transactions 2011, 40 (35) , 8800. https://doi.org/10.1039/c1dt10369e
    80. Zhong-Lin Lu, Xiao-Sheng Yang, Zhi-Fo Guo, Rui-Yao Wang. ( S )-4- tert -Butyl-2-phenyl-2-oxazoline derived palladacycles as efficient catalysts for the decomposition of P=S pesticides. Journal of Coordination Chemistry 2010, 63 (14-16) , 2659-2672. https://doi.org/10.1080/00958972.2010.491545
    81. Jairton Dupont, Fabricio R. Flores. Palladacycles in Catalysis. 2010, 319-342. https://doi.org/10.1002/9783527628698.hgc010
    82. Wei Jie Li, Sheng Xiang Qiu. A Novel D 2 ‐Symmetrical Chiral Tetraoxazoline Ligand for Highly Enantioselective Hydrosilylation of Aromatic Ketones. Advanced Synthesis & Catalysis 2010, 352 (7) , 1119-1122. https://doi.org/10.1002/adsc.201000018
    83. Xin-Qi Hao, Ya-Nan Wang, Jun-Rui Liu, Kun-Lun Wang, Jun-Fang Gong, Mao-Ping Song. Unsymmetrical, oxazolinyl-containing achiral and chiral NCN pincer ligand precursors and their complexes with palladium(II). Journal of Organometallic Chemistry 2010, 695 (1) , 82-89. https://doi.org/10.1016/j.jorganchem.2009.09.031
    84. Hisao Nishiyama, Jun-ichi Ito. Bis(oxazolinyl)phenyl transition-metal complexes: asymmetric catalysis and some reactions of the metals. Chem. Commun. 2010, 46 (2) , 203-212. https://doi.org/10.1039/B918923H
    85. Bart M. J. M. Suijkerbuijk, Daniël J. Schamhart, Huub Kooijman, Anthony L. Spek, Gerard van Koten, Robertus J. M. Klein Gebbink. Mono(NCN-pincer palladium)-metalloporphyrin catalysts: evidence for supramolecular bimetallic catalysis. Dalton Transactions 2010, 39 (27) , 6198. https://doi.org/10.1039/b925236n
    86. Gyandshwar Kumar Rao, Arun Kumar, Jahangeer Ahmed, Ajai Kumar Singh. Palladacycle containing nitrogen and selenium: highly active pre-catalyst for the Suzuki–Miyaura coupling reaction and unprecedented conversion into nano-sized Pd17Se15. Chemical Communications 2010, 46 (32) , 5954. https://doi.org/10.1039/c0cc01075h
    87. Youhei Umino, Hiroshi Nozaki, Hiroshi Hamana, Tadashi Narita. Novel anionic polyaddition of 2‐trifluoromethylacrylate by double Michael reaction with ethyl cyanoacetate. Journal of Polymer Science Part A: Polymer Chemistry 2009, 47 (21) , 5698-5708. https://doi.org/10.1002/pola.23613
    88. Shu Kobayashi, Ryosuke Matsubara. Catalytic Carbanion Reactions: Formation and Reaction of Carbanions from Ester or Amide Equivalents Using Catalytic Amounts of Bases. Chemistry – A European Journal 2009, 15 (41) , 10694-10700. https://doi.org/10.1002/chem.200901515
    89. Martin Bröring, Christian Kleeberg. A Cationic Chlorido‐bridged Palladium(II) Complex of the Sterically Hindered Bis(4‐methylthiazolyl)isoindoline Ligand (4‐Mebti). Zeitschrift für anorganische und allgemeine Chemie 2008, 634 (15) , 2793-2798. https://doi.org/10.1002/zaac.200800239
    90. Koichi Mitsudo, Tatsuhiko Imura, Takashi Yamaguchi, Hideo Tanaka. Preparation of a cationic bisoxazolinic nickel pincer catalyst and its applications to Michael addition and Mizoroki–Heck reaction. Tetrahedron Letters 2008, 49 (51) , 7287-7289. https://doi.org/10.1016/j.tetlet.2008.10.029
    91. Sascha Jautze, René Peters. Enantioselektive Dimetallkatalyse von Michael‐Additionen zur Bildung quartärer Stereozentren. Angewandte Chemie 2008, 120 (48) , 9424-9429. https://doi.org/10.1002/ange.200803539
    92. Sascha Jautze, René Peters. Enantioselective Bimetallic Catalysis of Michael Additions Forming Quaternary Stereocenters. Angewandte Chemie International Edition 2008, 47 (48) , 9284-9288. https://doi.org/10.1002/anie.200803539
    93. Relindis Y. Mawo, Diane M. Johnson, Irina P. Smoliakova. Synthesis of Pd(II) coordination complexes of (S)-4-isobutyl-2-methyl-2-oxazoline and (S)-2-(2,2-dimethylpropyl)-4-isopropyl-2-oxazoline. Inorganic Chemistry Communications 2008, 11 (11) , 1397-1400. https://doi.org/10.1016/j.inoche.2008.09.016
    94. Nilesh C. Mehendale, Martin Lutz, Anthony L. Spek, Robertus J.M. Klein Gebbink, Gerard van Koten. Self-assembly of para-OH functionalized ECE-metalated pincer complexes. Journal of Organometallic Chemistry 2008, 693 (18) , 2971-2981. https://doi.org/10.1016/j.jorganchem.2008.06.016
    95. Esteban P. Urriolabeitia. Oxidative Addition and Transmetallation. 2008, 35-67. https://doi.org/10.1002/9783527623211.ch3
    96. Juhanes Aydin, Andreas Rydén, Kálmán J. Szabó. Chiral palladium-pincer complex catalyzed asymmetric condensation of sulfonimines and isocyanoacetate. Tetrahedron: Asymmetry 2008, 19 (15) , 1867-1870. https://doi.org/10.1016/j.tetasy.2008.07.027
    97. Marcella Gagliardo, Nicklas Selander, Nilesh C. Mehendale, Gerard van Koten, Robertus J. M. Klein Gebbink, Kálmán J. Szabó. Catalytic Performance of Symmetrical and Unsymmetrical Sulfur‐Containing Pincer Complexes: Synthesis and Tandem Catalytic Activity of the First PCS‐Pincer Palladium Complex. Chemistry – A European Journal 2008, 14 (16) , 4800-4809. https://doi.org/10.1002/chem.200800350
    98. Ken Motokura, Mitsuru Tomita, Mizuki Tada, Yasuhiro Iwasawa. Acid–Base Bifunctional Catalysis of Silica–Alumina‐Supported Organic Amines for Carbon–Carbon Bond‐Forming Reactions. Chemistry – A European Journal 2008, 14 (13) , 4017-4027. https://doi.org/10.1002/chem.200702048
    99. Stephen M. Goldup, David A. Leigh, Paul J. Lusby, Roy T. McBurney, Alexandra M. Z. Slawin. Active Template Synthesis of Rotaxanes and Molecular Shuttles with Switchable Dynamics by Four‐Component Pd II ‐Promoted Michael Additions. Angewandte Chemie 2008, 120 (18) , 3429-3432. https://doi.org/10.1002/ange.200705859
    100. Stephen M. Goldup, David A. Leigh, Paul J. Lusby, Roy T. McBurney, Alexandra M. Z. Slawin. Active Template Synthesis of Rotaxanes and Molecular Shuttles with Switchable Dynamics by Four‐Component Pd II ‐Promoted Michael Additions. Angewandte Chemie International Edition 2008, 47 (18) , 3381-3384. https://doi.org/10.1002/anie.200705859
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