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Pure Appl. Chem., 2003, Vol. 75, No. 4, pp. 435-443

http://dx.doi.org/10.1351/pac200375040435

Carbenes. Pincers, chelates, and abnormal binding modes

R. H. Crabtree

225 Prospect St, New Haven, CT 06520-8107, USA

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  • Chen Shih-Ji, Lin Yuan-Deng, Chiang Yen-Hsin, Lee Hon Man: Rational Design of Ligand Precursors to Prepare Abnormal (Mesoionic) and Normal Carbene Complexes and Zwitterionic CX-Type Palladacycles (X = C, N). Eur. J. Inorg. Chem. 2014, 2014, 1492. <http://dx.doi.org/10.1002/ejic.201301465>
  • Xu Xiangya, Kim Seung Hyo, Zhang Xi, Das Atanu Kumar, Hirao Hajime, Hong Soon Hyeok: Abnormal N-Heterocyclic Carbene Gold(I) Complexes: Synthesis, Structure, and Catalysis in Hydration of Alkynes. Organometallics 2013, 32, 164. <http://dx.doi.org/10.1021/om3009603>
  • Ke Chun-Hung, Kuo Bing-Chiuan, Nandi Debkumar, Lee Hon Man: Monodentate Palladium Complexes Bearing Abnormal and Normal Carbene Ligands with a Formally Identical Steric Environment. Organometallics 2013, 32, 4775. <http://dx.doi.org/10.1021/om4004219>
  • Huckaba Aron J., Cao Bei, Hollis T. Keith, Valle Henry U., Kelly John T., Hammer Nathan I., Oliver Allen G., Webster Charles Edwin: Platinum CCC-NHC benzimidazolyl pincer complexes: synthesis, characterization, photostability, and theoretical investigation of a blue-green emitter. Dalton Trans. 2013, 42, 8820. <http://dx.doi.org/10.1039/c3dt50438g>
  • Peñafiel Itziar, Pastor Isidro M., Yus Miguel: Heck-Matsuda Reactions Catalyzed by a Hydroxyalkyl-Functionalized NHC and Palladium Acetate. Eur J Org 2012, 2012, 3151. <http://dx.doi.org/10.1002/ejoc.201200181>
  • Slamani Amel, Demir Serpil, Özdemir İsmail: Use of benzimidazolium salts for in situ generation of palladium catalysts in Heck reactions in water. Catalysis Communications 2012, 29, 141. <http://dx.doi.org/10.1016/j.catcom.2012.09.036>
  • Bates Joshua I., Gates Derek P.: 4-Phosphino-Substituted N-Heterocyclic Carbenes (NHCs) from the Abnormal Reaction of NHCs with Phosphaalkenes. Organometallics 2012, 31, 4529. <http://dx.doi.org/10.1021/om3003174>
  • Peñafiel Itziar, Pastor Isidro M., Yus Miguel, Esteruelas Miguel A., Oliván Montserrat, Oñate Enrique: (NHC)Palladium Complexes from Hydroxy-Functionalized Imidazolium Salts as Catalyst for the Microwave-Accelerated Fluorine-Free Hiyama Reaction. Eur J Org 2011, 2011, 7174. <http://dx.doi.org/10.1002/ejoc.201101110>
  • Boča Miroslav, Jameson Reginald F., Linert Wolfgang: Fascinating variability in the chemistry and properties of 2,6-bis-(benzimidazol-2-yl)-pyridine and 2,6-bis-(benzthiazol-2-yl)-pyridine and their complexes. Coord Chem Rev - 2011, 255, 290. <http://dx.doi.org/10.1016/j.ccr.2010.09.010>
  • Kronig Sabrina, Theuergarten Eileen, Holschumacher Dirk, Bannenberg Thomas, Daniliuc Constantin G., Jones Peter G., Tamm Matthias: Dihydrogen Activation by Frustrated Carbene-Borane Lewis Pairs: An Experimental and Theoretical Study of Carbene Variation. Inrog Chem 2011, 50, 7344. <http://dx.doi.org/10.1021/ic201290g>
  • Mrutu Agnes, Goldberg Karen I., Kemp Richard A.: Synthesis and characterization of a dinuclear Ni complex containing a bridging CNC pincer ligand. Inorg Chim Ada 2010, 364, 115. <http://dx.doi.org/10.1016/j.ica.2010.08.049>
  • Ghadwal Rajendra S., Roesky Herbert W., Granitzka Markus, Stalke Dietmar: A Facile Route to Functionalized N-Heterocyclic Carbenes (NHCs) with NHC Base-Stabilized Dichlorosilylene. J Am Chem Soc 2010, 132, 10018. <http://dx.doi.org/10.1021/ja104386g>
  • Inés Blanca, SanMartin Raul, Moure María Jesús, Domínguez Esther: Insights into the Role of New Palladium Pincer Complexes as Robust and Recyclable Precatalysts for Suzuki-Miyaura Couplings in Neat Water. Adv Synth Catal 2009, 351, 2124. <http://dx.doi.org/10.1002/adsc.200900345>
  • Bates Joshua I., Kennepohl Pierre, Gates Derek P.: Abnormal Reactivity of an N-Heterocyclic Carbene (NHC) with a Phosphaalkene: A Route to a 4-Phosphino-Substituted NHC. angew chemie 2009, 121, 10028. <http://dx.doi.org/10.1002/ange.200905401>
  • Bates Joshua I., Kennepohl Pierre, Gates Derek P.: Abnormal Reactivity of an N-Heterocyclic Carbene (NHC) with a Phosphaalkene: A Route to a 4-Phosphino-Substituted NHC. Angew Chem Int Ed 2009, 48, 9844. <http://dx.doi.org/10.1002/anie.200905401>
  • Corberán Rosa, Mas-Marzá Elena, Peris Eduardo: Mono-, Bi- and Tridentate N-Heterocyclic Carbene Ligands for the Preparation of Transition-Metal-Based Homogeneous Catalysts. Eur J Inorg Chem 2009, 2009, 1700. <http://dx.doi.org/10.1002/ejic.200801095>
  • Zeng Xiaoming, Frey Guido D., Kinjo Rei, Donnadieu Bruno, Bertrand Guy: Synthesis of a Simplified Version of Stable Bulky and Rigid Cyclic (Alkyl)(amino)carbenes, and Catalytic Activity of the Ensuing Gold(I) Complex in the Three-Component Preparation of 1,2-Dihydroquinoline Derivatives. J Am Chem Soc 2009, 131, 8690. <http://dx.doi.org/10.1021/ja902051m>
  • Holschumacher Dirk, Taouss Christina, Bannenberg Thomas, Hrib Cristian G., Daniliuc Constantin G., Jones Peter G., Tamm M.: Dehydrogenation reactivity of a frustrated carbene–borane Lewis pair. Dalton Trans 2009, 6927. <http://dx.doi.org/10.1039/b908074k>
  • Hahn F. Ekkehardt, Jahnke Mareike C.: Heterocyclische Carbene – Synthese und Koordinationschemie. Angew Chem 2008, 120, 3166. <http://dx.doi.org/10.1002/ange.200703883>
  • Holschumacher Dirk, Bannenberg Thomas, Hrib Cristian G., Jones Peter G., Tamm Matthias: Heterolytic Dihydrogen Activation by a Frustrated Carbene-Borane Lewis Pair. Angew Chem 2008, 120, 7538. <http://dx.doi.org/10.1002/ange.200802705>
  • Hahn F. Ekkehardt, Jahnke Mareike C.: Heterocyclic Carbenes: Synthesis and Coordination Chemistry. Angew Chem Int Ed 2008, 47, 3122. <http://dx.doi.org/10.1002/anie.200703883>
  • Holschumacher Dirk, Bannenberg Thomas, Hrib Cristian G., Jones Peter G., Tamm Matthias: Heterolytic Dihydrogen Activation by a Frustrated Carbene-Borane Lewis Pair. Angew Chem Int Ed 2008, 47, 7428. <http://dx.doi.org/10.1002/anie.200802705>
  • Busetto Luigi, Cristina Cassani M., Femoni Cristina, Macchioni Alceo, Mazzoni Rita, Zuccaccia Daniele: Synthesis, molecular structures and solution NMR studies of N-heterocyclic carbene–amine silver complexes. J Organomet Chem 2008, 693, 2579. <http://dx.doi.org/10.1016/j.jorganchem.2008.04.030>
  • Song Guoyong, Li Yongxin, Chen Shanshan, Li Xingwei: Hydrogen bonding-assisted tautomerization of pyridine moieties in the coordination sphere of an Ir(i) complex. Chem Commun 2008, 3558. <http://dx.doi.org/10.1039/b804931a>
  • Arnold Polly L., Wilson Claire: Sterically demanding bi- and tridentate alkoxy-N-heterocyclic carbenes. Inorg Chim Ada 2007, 360, 190. <http://dx.doi.org/10.1016/j.ica.2006.07.075>
  • Hahn Ekkehardt F., Heidrich Beate, Hepp Alexander, Pape Tania: Coordination compounds of N,N′-olefin functionalized imidazolin-2-ylidenes. J Organomet Chem 2007, 692, 4630. <http://dx.doi.org/10.1016/j.jorganchem.2007.04.025>
  • Lloyd-Jones Guy C., Alder Roger W., Owen-Smith Gareth J. J.: Intermolecular Insertion of an N,N-Heterocyclic Carbene into a Nonacidic CH Bond: Kinetics, Mechanism and Catalysis by (K-HMDS)2 (HMDS=Hexamethyldisilazide). Chem Eur J 2006, 12, 5361. <http://dx.doi.org/10.1002/chem.200600266>
  • Mas-Marzá Elena, Reis Patrícia M., Peris Eduardo, Royo Beatriz: Dioxomolybdenum(VI) complexes containing N-heterocyclic carbenes. J Organomet Chem 2006, 691, 2708. <http://dx.doi.org/10.1016/j.jorganchem.2006.02.004>
  • Wang Zhi-Guo, Sun Hong-Mei, Yao Hai-Sheng, Yao Ying-Ming, Shen Qi, Zhang Yong: Bis-aryloxo-functionalized NHC complexes of ytterbium(III): Syntheses and structures of Yb[O-4,6-tBu2-C6H2-2-CH2{C(RNCHCHN)}]2N(iPr)2 (R=iPr, Me). J Organomet Chem 2006, 691, 3383. <http://dx.doi.org/10.1016/j.jorganchem.2006.04.029>
  • Herndon James W.: The chemistry of the carbon-transition metal double and triple bond: annual survey covering the year 2003. Coord Chem Rev - 2005, 249, 999. <http://dx.doi.org/10.1016/j.ccr.2004.10.009>
  • Jones Nathan D., Cavell Ronald G.: Phosphorus-substituted carbene complexes: Chelates, pincers and spirocycles. J Organomet Chem 2005, 690, 5485. <http://dx.doi.org/10.1016/j.jorganchem.2005.09.024>
  • Graham David C., Cavell Kingsley J., Yates Brian F.: Influence of geometry on reductive elimination of hydrocarbyl–palladium–carbene complexes. Dalton Trans 2005, 1093. <http://dx.doi.org/10.1039/b417111j>
  • Magill Alison M., Yates Brian F.: An Assessment of Theoretical Protocols for Calculation of the pKa Values of the Prototype Imidazolium Cation. Aust J Chem 2004, 57, 1205. <http://dx.doi.org/10.1071/CH04159>
  • Crabtree Robert H.: Carbenes. Pincers, Chelates, and Abnormal Binding Modes. ChemInform 2003, 34. <http://dx.doi.org/10.1002/chin.200345223>