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Journal articles on the topic 'Migratory-insertion reactions'

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Published: 4 June 2021
Last updated: 17 February 2022

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1

Adeyemi, Olalere G., and Neil J. Coville. "Solvent-Free Organometallic Migratory Insertion Reactions." Organometallics 22, no. 11 (May 2003): 2284–90. http://dx.doi.org/10.1021/om0301738.

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2

Xia, Ying, Yan Zhang, and Jianbo Wang. "Catalytic Cascade Reactions Involving Metal Carbene Migratory Insertion." ACS Catalysis 3, no. 11 (October 22, 2013): 2586–98. http://dx.doi.org/10.1021/cs4006666.

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3

Zeidan, Nicolas, and Mark Lautens. "Migratory Insertion Strategies for Dearomatization." Synthesis 51, no. 22 (August 26, 2019): 4137–46. http://dx.doi.org/10.1055/s-0037-1611918.

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Development of strategies for molecule functionalization by dearomatization has surged in the last two decades. The benefits of overcoming the resonance stabilization energy outweigh the cost; diverse compounds could be accessed in a short number of steps. One approach that has been of interest in recent years is the dearomatization of indoles and other (hetero)aromatic compounds by migratory insertion. The chiral σ-bond palladium intermediate could be reduced or trapped by a second functionalization. In this short review we will summarize the recently discovered reactions from our group and others in this field of metal-catalyzed dearomatizations by migratory insertion.1 Introduction2 Monofunctionalizations: Heck and Reductive Heck Reactions2.1 N-Tethered Heterocycles2.2 Non-N-tethered Heterocycles2.3 Non-heterocycles3 Dearomative Difunctionalizations: Interrupted Heck Reaction3.1 N-Tethered Heterocycles3.2 Non-N-tethered Heterocycles4 Conclusion
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4

Walewska, Małgorzata, Judith Baumgartner, and Christoph Marschner. "1,2- and 1,1-Migratory Insertion Reactions of Silylated Germylene Adducts." Molecules 25, no. 3 (February 6, 2020): 686. http://dx.doi.org/10.3390/molecules25030686.

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The reactions of the PMe3 adduct of the silylated germylene [(Me3Si)3Si]2Ge: with GeCl2·dioxane were found to yield 1,1-migratory insertion products of GeCl2 into one or two Ge–Si bonds. In a related reaction, a germylene was inserted with tris(trimethylsilyl)silyl and vinyl substituents into a Ge–Cl bond of GeCl2. This was followed by intramolecular trimethylsilyl chloride elimination to another cyclic germylene PMe3 adduct. The reaction of the GeCl2 mono-insertion product (Me3Si)3SiGe:GeCl2Si(SiMe3)3 with Me3SiC≡CH gave a mixture of alkyne mono- and diinsertion products. While the reaction of a divinylgermylene with GeCl2·dioxane only results in the exchange of the dioxane of GeCl2 against the divinylgermylene as base, the reaction of [(Me3Si)3Si]2Ge: with one GeCl2·dioxane and three phenylacetylenes gives a trivinylated germane with a chlorogermylene attached to one of the vinyl units.
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5

DeLuca, Ryan J., Benjamin J. Stokes, and Matthew S. Sigman. "The strategic generation and interception of palladium-hydrides for use in alkene functionalization reactions." Pure and Applied Chemistry 86, no. 3 (March 20, 2014): 395–408. http://dx.doi.org/10.1515/pac-2014-5041.

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Abstract We review methods that our lab has developed for the generation of Pd-hydrides and the manipulation of these useful intermediates via β-hydride elimination and migratory insertion steps. For a given alkene functionalization reaction, careful understanding of the dynamics of β-hydride elimination, migratory insertion, and transmetallation have allowed for the selective functionalization of Pd-alkyl intermediates. This has afforded us a means by which to transpose palladium to a desired position on a substrate for subsequent functionalization, empowering a number of useful C–H, C–O, and C–C bond-forming reactions.
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6

Fernández-Galán, Rafael, Antonio Antiñolo, Fernando Carrillo-Hermosilla, Isabel López-Solera, Antonio Otero, Amparo Serrano-Laguna, and Elena Villaseñor. "Migratory Insertion Reactions in Asymmetrical Guanidinate-Supported Zirconium Complexes." Organometallics 31, no. 23 (November 29, 2012): 8360–69. http://dx.doi.org/10.1021/om300942p.

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7

Xia, Ying, Yan Zhang, and Jianbo Wang. "ChemInform Abstract: Catalytic Cascade Reactions Involving Metal Carbene Migratory Insertion." ChemInform 45, no. 2 (December 19, 2013): no. http://dx.doi.org/10.1002/chin.201402237.

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8

Mazzacano, Thomas J., Noel J. Leon, Greyson W. Waldhart, and Neal P. Mankad. "Fundamental organometallic chemistry under bimetallic influence: driving β-hydride elimination and diverting migratory insertion at Cu and Ni." Dalton Transactions 46, no. 17 (2017): 5518–21. http://dx.doi.org/10.1039/c6dt04533b.

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9

BI, SIWEI, JUNFENG ZHAO, WEI FAN, and PING LI. "A DFT STUDY OF CO MIGRATORY INSERTION REACTIONS WITH A NEW TYPE OF GROUP 10 METAL-ALKYL AND METAL-ALKOXIDE BONDS." Journal of Theoretical and Computational Chemistry 11, no. 01 (February 2012): 1–17. http://dx.doi.org/10.1142/s0219633612500010.

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The CO migratory insertion into M–O and M–C bonds of the new model (PMe3)2M(η2 – CH2CH2O) ( M = Ni , Pd and Pt ) (model (d)) proposed in this work has been studied with the aid of density functional theory (DFT) calculations. It is found (1) when M = Ni , CO migratory insertion into Ni–C is thermodynamically and kinetically favored, and (2) when M = Pd and Pt , the insertion into M–O bond via a one-step process is preferred. Further investigation on CO migratory insertion using Pt(PMe3)2(C7H10O) (R′-Pt) derived from the experimental compound Pt(PEt3)2(C7H10O) gives the same conclusions as model (d) with M = Pt . Results obtained from the reaction of model (d) ( M = Pt ) with CO are consistent with the experimental observation that CO prefers to insert into Pt–O bond of Pt(PEt3)2(C7H10O) .
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10

Paraja, Miguel, and Carlos Valdés. "Pd-catalyzed cascade reactions between o-iodo-N-alkenylanilines and tosylhydrazones: novel approaches to the synthesis of polysubstituted indoles and 1,4-dihydroquinolines." Chemical Communications 52, no. 37 (2016): 6312–15. http://dx.doi.org/10.1039/c6cc01880g.

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11

Espinosa, Arturo, Edgar de las Heras, and Rainer Streubel. "Oxaphosphirane-Borane Complexes: Ring Strain and Migratory Insertion/Ring-Opening Reactions." Inorganic Chemistry 53, no. 12 (June 5, 2014): 6132–40. http://dx.doi.org/10.1021/ic500536h.

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12

Ilg, Kerstin, and Helmut Werner. "Substitution and Migratory Insertion Reactions of Square-Planar Allenylidene Iridium Complexes†." Organometallics 20, no. 17 (August 2001): 3782–94. http://dx.doi.org/10.1021/om010353m.

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13

Foo, Thomas, and Robert G. Bergman. "Migratory insertion reactions of indenyliridium dialkyls and alkyl and aryl hydrides." Organometallics 11, no. 5 (May 1992): 1811–19. http://dx.doi.org/10.1021/om00041a014.

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14

van Leeuwen, Piet W. N. M., and Kees F. Roobeek. "The Cossee mechanism: Migratory insertion reactions in palladium phosphine-phosphinite complexes." Recueil des Travaux Chimiques des Pays-Bas 114, no. 2 (September 2, 2010): 73–75. http://dx.doi.org/10.1002/recl.19951140206.

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15

Zhao, Huaxin, Guobin Ma, Xiaojuan Xie, Yong Wang, Jian Hao, and Wen Wan. "Pd(ii)-Catalyzed decarboxylative meta-C–H difluoromethylation." Chemical Communications 55, no. 27 (2019): 3927–30. http://dx.doi.org/10.1039/c9cc00984a.

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Palladium(ii)-catalyzed decarboxylative meta-C–H difluoromethylation reactions have been developed. Initial mechanistic studies disclosed that a migratory insertion would be involved in this meta-selective C–H functionalization.
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16

Albéniz, Ana C., Pablo Espinet, and Alberto Pérez-Mateo. "Palladium(II) allylic complexes by carbene transmetalation and migratory insertion reactions: Synthesis and side reactions." Journal of Organometallic Chemistry 695, no. 3 (February 2010): 441–45. http://dx.doi.org/10.1016/j.jorganchem.2009.10.027.

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17

Pan, Chongqing, Si-Yong Yin, Qing Gu, and Shu-Li You. "CpxM(iii)-catalyzed enantioselective C–H functionalization through migratory insertion of metal–carbenes/nitrenes." Organic & Biomolecular Chemistry 19, no. 34 (2021): 7264–75. http://dx.doi.org/10.1039/d1ob01248g.

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In this review, we highlight the developments in chiral CpxM(iii) complexes or achiral CpxM(iii) complexes/chiral carboxylic acid-catalyzed enantioselective C–H functionalization reactions through migratory insertion of metal–carbenes/nitrenes.
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18

Anderson, Laura L., Joseph A. R. Schmidt, John Arnold, and Robert G. Bergman. "Neutral and Cationic Alkyl Tantalum Imido Complexes: Synthesis and Migratory Insertion Reactions." Organometallics 25, no. 14 (July 2006): 3394–406. http://dx.doi.org/10.1021/om060081t.

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19

Herber, Ulrich, Rita Guerrero Sanchez, Olaf Gevert, Matthias Laubender, and Helmut Werner. "PX3-induced migratory insertion reactions of half-sandwich-type carbenerhodium(I) complexes." New Journal of Chemistry 25, no. 3 (2001): 396–99. http://dx.doi.org/10.1039/b008601k.

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20

Collins, Lee R., Gabriele Hierlmeier, Mary F. Mahon, Ian M. Riddlestone, and Michael K. Whittlesey. "Unexpected Migratory Insertion Reactions of M(alkyl)2 (M=Zn, Cd) and Diamidocarbenes." Chemistry - A European Journal 21, no. 8 (January 8, 2015): 3215–18. http://dx.doi.org/10.1002/chem.201406406.

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21

Galajov, Miguel, Carlos García, Manuel Gómez, and Pilar Gómez-Sal. "Trialkyl imido niobium and tantalum compounds: synthesis, structural study and migratory insertion reactions." Dalton Transactions 40, no. 12 (2011): 2797. http://dx.doi.org/10.1039/c0dt01449d.

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22

Elorriaga, David, Fernando Carrillo-Hermosilla, Antonio Antiñolo, Isabel López-Solera, Bérengère Menot, Rafael Fernández-Galán, Elena Villaseñor, and Antonio Otero. "New Alkylimido Niobium Complexes Supported by Guanidinate Ligands: Synthesis, Characterization, and Migratory Insertion Reactions." Organometallics 31, no. 5 (February 24, 2012): 1840–48. http://dx.doi.org/10.1021/om201192w.

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23

Haynes, Anthony, Jean M. Pearson, Paul W. Vickers, Jonathan P. H. Charmant, and Peter M. Maitlis. "Model reactions of a carbonylation catalyst: phosphite induced migratory CO insertion in [MeIr(CO)2I3]−." Inorganica Chimica Acta 270, no. 1-2 (April 1998): 382–91. http://dx.doi.org/10.1016/s0020-1693(97)05872-6.

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24

Rampersad, Marilyn V., Erik Zuidema, Jan Meine Ernsting, Piet W. N. M. van Leeuwen, and Marcetta Y. Darensbourg. "CO and Ethylene Migratory Insertion Reactions and Copolymerization Involving Palladium Complexes of a NiN2S2Metallodithiolate Ligand." Organometallics 26, no. 4 (February 2007): 783–92. http://dx.doi.org/10.1021/om0605783.

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25

Ortiz de la Tabla, Laura, Inmaculada Matas, Eleuterio Álvarez, Pilar Palma, and Juan Cámpora. "Migratory insertion reactions of nickel and palladium σ-alkyl complexes with a phosphinito-imine ligand." Dalton Transactions 41, no. 48 (2012): 14524. http://dx.doi.org/10.1039/c2dt31334k.

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26

Macgregor, Stuart A., and Greg W. Neave. "Theoretical Study of CO Migratory Insertion Reactions with Group 10 Metal−Alkyl and −Alkoxide Bonds." Organometallics 22, no. 22 (October 2003): 4547–56. http://dx.doi.org/10.1021/om030459c.

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27

Albéniz, Ana C. "Reactive Palladium Carbenes: Migratory Insertion and Other Carbene-Hydrocarbyl Coupling Reactions on Well-Defined Systems." European Journal of Inorganic Chemistry 2018, no. 33 (July 19, 2018): 3693–705. http://dx.doi.org/10.1002/ejic.201800597.

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28

Colletti, Steven L., and Ronald L. Halterman. "Asymmetric migratory insertion reactions of the chiral [(binaphthyldiyldimethylene)cyclopentadienyl]iron complex (BpDMCp)Fe(CO)2CH3." Organometallics 11, no. 2 (February 1992): 980–83. http://dx.doi.org/10.1021/om00038a076.

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29

Rix, Francis C., and Maurice Brookhart. "Energetics of Migratory Insertion Reactions in Pd(II) Acyl Ethylene, Alkyl Ethylene, and Alkyl Carbonyl Complexes." Journal of the American Chemical Society 117, no. 3 (January 1995): 1137–38. http://dx.doi.org/10.1021/ja00108a034.

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30

Vahabi, Amir Hossein, Abdolali Alizadeh, Hamid Reza Khavasi, and Ayoob Bazgir. "Palladium-Catalyzed Migratory Insertion of Isocyanides into C(thiophene)-SMe Bonds: Access to Atom-Transfer Reactions." European Journal of Organic Chemistry 2017, no. 36 (September 26, 2017): 5347–56. http://dx.doi.org/10.1002/ejoc.201701026.

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31

Hartwig, John F., Robert G. Bergman, and Richard A. Andersen. "Oxygen- and carbon-bound ruthenium enolates: migratory insertion, reductive elimination, .beta.-hydrogen elimination, and cyclometalation reactions." Organometallics 10, no. 9 (September 1991): 3326–44. http://dx.doi.org/10.1021/om00055a060.

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32

Braunstein, Pierre, Michael Knorr, and Thomas Stährfeldt. "Heterobimetallic templates for Carbon–Carbon bond formation by migratory insertion reactions involving CO, isonitriles or olefins." J. Chem. Soc., Chem. Commun., no. 17 (1994): 1913–14. http://dx.doi.org/10.1039/c39940001913.

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33

Negishi, Eiichi, Kazunari Akiyoshi, Brian O'Connor, Kentaro Takagi, and Guangzhong Wu. "Migratory insertion reactions of organometallics. 3. Carbon-carbon bond forming reactions of organotransition metals with .alpha.- or .gamma.-haloorganolithium reagents." Journal of the American Chemical Society 111, no. 8 (April 1989): 3089–91. http://dx.doi.org/10.1021/ja00190a067.

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34

Su, Qian, Jipeng Ding, Zhihui Du, Yunrong Lai, Hongzuo Li, Ming-An Ouyang, Liyan Song, and Ran Lin. "Recent Advances in the Reactions of Cyclic Carbynes." Molecules 25, no. 21 (October 30, 2020): 5050. http://dx.doi.org/10.3390/molecules25215050.

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The acyclic organic alkynes and carbyne bonds exhibit linear shapes. Metallabenzynes and metallapentalynes are six- or five-membered metallacycles containing carbynes, whose carbine-carbon bond angles are less than 180°. Such distortion results in considerable ring strain, resulting in the unprecedented reactivity compared with acyclic carbynes. Meanwhile, the aromaticity of these metallacycles would stabilize the ring system. The fascinating combination of ring strain and aromaticity would lead to interesting reactivities. This mini review summarized recent findings on the reactivity of the metal–carbon triple bonds and the aromatic ring system. In the case of metallabenzynes, aromaticity would prevail over ring strain. The reactions are similar to those of organic aromatics, especially in electrophilic reactions. Meanwhile, fragmentation of metallacarbynes might be observed via migratory insertion if the aromaticity of metallacarbynes is strongly affected. In the case of metallapentalynes, the extremely small bond angle would result in high reactivity of the carbyne moiety, which would undergo typical reactions for organic alkynes, including interaction with coinage metal complexes, electrophilic reactions, nucleophilic reactions and cycloaddition reactions, whereas the strong aromaticity ensured the integrity of the bicyclic framework of metallapentalynes throughout all reported reaction conditions.
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35

Liu, Bo, and Sheng Fu Ji. "Effect of H2 in CO Feed Gas on Carbonylation of Methanol to Acetic Acid over Ir-Ru Catalysts." Advanced Materials Research 610-613 (December 2012): 2600–2605. http://dx.doi.org/10.4028/www.scientific.net/amr.610-613.2600.

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Effect of the minor H2 presence in CO feed gas on the carbonylation of methanol to acetic acid over homogeneous Ir-Ru catalysts was studied. The results indicated that the carbonylation reaction rate would be decreased with the increasing of H2 content in CO feed gas. The process of CO migratory insertion was inhibited with the decrease of CO partial pressure in feed gas. With the increasing of H2 content in CO feed gas, CH4 composition distribution in gas byproducts was increased while that of CO2 was decreased. The yield of propionic acid in liquid products was increased. The occurrence extent of hydrogenated side reactions was affected due to minor H2 presence.
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36

Wang, Jianbo, and Kang Wang. "Transition-Metal-Catalyzed Cross-Coupling with Non-Diazo Carbene Precursors." Synlett 30, no. 05 (October 16, 2018): 542–51. http://dx.doi.org/10.1055/s-0037-1611020.

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Transition-metal-catalyzed cross-coupling reactions through metal carbene migratory insertion have emerged as powerful methodology for carbon–carbon bond constructions. Typically, diazo compounds (or in situ generated diazo compounds from N-tosylhydrazones) have been employed as the metal carbene precursors for this type of cross-coupling reactions. Recently, cross-coupling reactions employing non-diazo carbene precursors, such as conjugated ene-yne-ketones, allenyl ketones, alkynes, cyclopropenes, and Cr(0) Fischer carbenes, have been developed. This account will summarize our efforts in the development of transition-metal-catalyzed cross-coupling reactions with these non-diazo carbene precursors.1 Introduction2 Cross-Coupling with Ene-yne-ketones, Allenyl Ketones, and Alkynes3 Cross-Coupling Involving Ring-Opening of Cyclopropenes4 Palladium-Catalyzed Cross-Coupling with Chromium(0) Fischer Carbenes5 Conclusion
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37

Kocienski, Philip, and Nicholas J. Dixon. "Stereoselective Synthesis of Homoallylic Alcohols by Migratory Insertion Reactions of Higher-Order Cyanocuprates and Nickel-Catalysed Coupling Reactions Involving Enol Carbamates." Synlett 1989, no. 01 (1989): 52–54. http://dx.doi.org/10.1055/s-1989-20354.

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38

Kocienski, Philip, and Nicholas Dixon. "Stereoselective Synthesis of Homoallylic Alcohols by Migratory Insertion Reactions of Higher-Order Cyanocuprates and Nickel-Catalysed Coupling Reactions Involving Enol Carbamates." Synlett 1989, no. 1 (January 1989): 52–54. http://dx.doi.org/10.1055/s-1989-34703.

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39

Brookhart, M., and D. M. Lincoln. "Comparison of migratory aptitudes of hydride and alkyl groups in .beta.-migratory insertion reactions of Cp*(P(OMe)3)Rh(C2H4)R+ (R = H, CH2CH3)." Journal of the American Chemical Society 110, no. 26 (December 1988): 8719–20. http://dx.doi.org/10.1021/ja00234a036.

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40

Werner, Helmut, Ralf Wiedemann, Matthias Laubender, Bettina Windmüller, and Justin Wolf. "An Unprecedented Type of Migratory Insertion Reactions of Unsaturated C3 Units into Rh−O and Rh−C Bonds." Chemistry 7, no. 9 (May 4, 2001): 1959–67. http://dx.doi.org/10.1002/1521-3765(20010504)7:9<1959::aid-chem1959>3.0.co;2-7.

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41

Burkhardt, Elizabeth R., Jeffrey J. Doney, Robert G. Bergman, and Clayton H. Heathcock. "Tungsten and molybdenum 2-oxaallyl [.eta.1-(C)-enolate] complexes: functional group transformations, photochemical aldol reactions, and alkyne/carbon monoxide migratory insertion reactions." Journal of the American Chemical Society 109, no. 7 (April 1987): 2022–39. http://dx.doi.org/10.1021/ja00241a020.

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42

Pérez-Jiménez, Marina, Jesús Campos, Joaquín López-Serrano, and Ernesto Carmona. "Reactivity of a trans-[H–MoMo–H] unit towards alkenes and alkynes: bimetallic migratory insertion, H-elimination and other reactions." Chemical Communications 54, no. 66 (2018): 9186–89. http://dx.doi.org/10.1039/c8cc04945a.

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43

Bai, Wei, Ka-Ho Lee, Jiangxi Chen, Herman H. Y. Sung, Ian D. Williams, Zhenyang Lin, and Guochen Jia. "Reactions of (Cyclopentadienylidenehydrazono)triphenylphosphorane with Chlororuthenium(II) Complexes and Substituent Effect on the Thermodynamic Trend in the Migratory-Insertion Reactions of Chlororuthenium–Alkylidene Complexes." Organometallics 36, no. 17 (August 29, 2017): 3266–75. http://dx.doi.org/10.1021/acs.organomet.7b00427.

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44

Werner, Helmut, Kerstin Ilg, and Birgit Weberndörfer. "Synthesis and Migratory Insertion Reactions of (Vinylidene)iridium Complexestrans-[IrX(CCRR‘)(PiPr3)2] Containing Alkyl, Aryl, Alkynyl, and Azide Ligands†,1." Organometallics 19, no. 16 (August 2000): 3145–53. http://dx.doi.org/10.1021/om990874y.

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45

Louie, Brenda M., Steven J. Rettig, Alan Storr, and James Trotter. "Syntheses and reactivity of square-planar Rh(I) complexes, LRh(CO) (L = unsymmetric tridentate chelating pyrazolylgallate ligand). X-ray crystal structures of [Me2Gapz(OCH2CH2NH2)]Rh(CO) and [Me2Gapz(OCH2CH2NMe2)]Rh(COMe)I (pz = pyrazolyl, N2C3H3)." Canadian Journal of Chemistry 63, no. 11 (November 1, 1985): 3019–26. http://dx.doi.org/10.1139/v85-501.

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The syntheses and characterization of a number of square-planar Rh(I) monocarbonyl complexes incorporating un-symmetrical, tridentate, pyrazolylgallate ligands in a meridional coordination mode are described. Oxidative addition reactions of these complexes are detailed and a facile migratory insertion reaction, following the addition of methyl iodide, has resulted in a five-coordinate square-pyramidal Rh(III) acetyl complex. Crystal structures of two compounds are presented, [Me2Gapz(OCH2CH2NH2)]Rh(CO) and [Me2Gapz(OCH2CH2NMe2)]Rh(COMe)I, and confirm the molecular arrangements predicted on the basis of other physical measurements. Crystals of the former are monoclinic, a = 10.212(2), b = 7.8484(5), c = 16.733(2) Å, β = 105.133(6)°, z = 4, space group P21/c; and those of the latter are monoclinic, a = 10.0960(11), b = 11.5352(8), c = 15.871(2) Å, β = 105.764(6)°, z = 4, space group P21/n. Both structures were solved by conventional heavy atom methods and were refined by full-matrix least-square procedures to R = 0.026 and 0.036, respectively, for 2142 and 2941 reflections with I ≥ 3σ(I).
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46

Stockland Jr., Robert A., Gordon K. Anderson, Nigam P. Rath, Janet Braddock-Wilking, and J. Christopher Ellegood. "Synthesis of the complexes [PdCIR(cod)] (R = benzyl, ethyl; cod = 1,5-cyclooctadiene). β-Elimination from [PdCIEt(cod)] to give the η1,η2 and η3 isomers of [Pd2(μ-Cl)2(C8H13)2]." Canadian Journal of Chemistry 74, no. 11 (November 1, 1996): 1990–97. http://dx.doi.org/10.1139/v96-226.

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Treatment of [PdCl2(cod)] with tetrabenzyltin gives the benzylpalladium complex [PdCl(CH2Ph)(cod)] (cod = 1,5-cyclooctadiene), 1a, whose structure has been determined by X-ray crystallography. It adopts approximate square-planar geometry, with the double bonds perpendicular to the square plane. The corresponding ethylpalladium derivative 1b has been prepared by a similar method, but it is considerably less stable. It decomposes by (β-elimination to produce ethene and a transient hydride complex, which either undergoes migratory insertion to give [Pd2(μ-Cl)2(η1,η2-C8H13)2], 2a, or dinuclear reductive elimination with a second molecule of 1b to produce ethane, [PdCl2(cod)], free cyclooctadiene, and palladium metal. Complex 2a has also been prepared by reaction of [PdCl2(cod)] with NaBH4. At higher temperatures 2a converts to an equilibrium mixture with its η3-allyl isomer, 2b. Reactions of [PdCl2(cod)] or K2PdCl4 in the presence of cyclooctadiene in aqueous solution to produce 2a or 2b have also been investigated. Key words: palladium, diene complexes, allyl complexes, isomerization, β-elimination.
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47

Antwi-Nsiah, Frederick H., Okemona Oke, and Martin Cowie. "Heterobinuclear Alkyl Complexes of Rhodium and Iridium. Migratory Insertion or Ir-to-Rh Migration of a Methyl Group in Reactions with Small Molecules." Organometallics 15, no. 3 (January 1996): 1042–54. http://dx.doi.org/10.1021/om9505874.

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48

McGhee, William D., and Robert G. Bergman. "Synthesis of an (.eta.3-allyl)(hydrido)iridium complex and its reactions with arenes and alkanes. Sequential intermolecular carbon-hydrogen oxidative addition and hydride-to-alkene migratory insertion reactions." Journal of the American Chemical Society 110, no. 13 (June 1988): 4246–62. http://dx.doi.org/10.1021/ja00221a026.

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49

Shultz, C. Scott, John Ledford, Joseph M. DeSimone, and Maurice Brookhart. "Kinetic Studies of Migratory Insertion Reactions at the (1,3-Bis(diphenylphosphino)propane)Pd(II) Center and Their Relationship to the Alternating Copolymerization of Ethylene and Carbon Monoxide." Journal of the American Chemical Society 122, no. 27 (July 2000): 6351–56. http://dx.doi.org/10.1021/ja994251n.

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50

Rahaman, Ahibur, Fakir Rafiqul Alam, Shishir Ghosh, Derek A. Tocher, Matti Haukka, Shariff E. Kabir, Ebbe Nordlander, and Graeme Hogarth. "Reactions of the σ,π-furyl complex [Fe2(CO)6(μ-Fu)(μ-PFu2)] (Fu = C4H3O) with phosphines: Carbonyl substitution, migratory carbonyl insertion and cyclometallation-induced furan elimination." Journal of Organometallic Chemistry 751 (February 2014): 326–35. http://dx.doi.org/10.1016/j.jorganchem.2013.05.026.

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