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Journal articles on the topic 'Organoindium'

Author: Grafiati
Published: 4 June 2021
Last updated: 7 February 2022

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1

Singh, Atul. "Organoindium Reagents." Synlett 24, no. 11 (June 10, 2013): 1457–58. http://dx.doi.org/10.1055/s-0033-1339287.

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2

Zambroń, Bartosz K. "Internal Chelation within Functionalized Organoindium Reagents: Prospects for Regio- and Stereocontrol in the Allylation, Propargylation and Allenylation of Carbonyl Compounds." Synthesis 52, no. 08 (February 17, 2020): 1147–80. http://dx.doi.org/10.1055/s-0039-1690817.

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The low basicity, selective nucleophilicity, and mildness of organoindium compounds allow for the incorporation of many important yet sensitive functional groups into their structure, including examples capable of intramolecularly chelating the indium center within these reagents. The specific nature of such chelated organoindiums causes the reactions involving them to proceed in a unique manner, often with regio- and stereoselectivity inaccessible with simple organometallic reagents. This review covers the rare examples of regio- and stereoselective allylation, propargylation, and allenylation of carbonyl compounds with chelated organoindiums, including brief descriptions of the applications of the resulting adducts in the asymmetric synthesis of natural products and synthetic targets of biological and medicinal interest.1 Introduction2 Internal Chelation Control in the Allylation Processes2.1 Allylindiums with a Chelating Center at the γ-Position2.2 Allylindiums with a chelating Center at the δ-Position2.3 Allylindiums with a Chelating Center at ε- and ζ-Positions2.4 Allylindiums with a Chelating Center at γ′- and δ′-Positions3 Internal Chelation Control in Propargylation and Allenylation Processes­3.1 Additions of Chelated Allenylindiums3.2 Additions of Chelated Propargylindiums4 Conclusion
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3

Cowley, Alan H., François P. Gabbaï, Harold S. Isom, Andreas Decken, and Robert D. Culp. "Structural Diversity in Organoindium Iodides." Main Group Chemistry 1, no. 1 (September 1995): 9–19. http://dx.doi.org/10.1080/13583149512331338225.

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4

Zhao, Kai, Liang Shen, Zhi-Liang Shen, and Teck-Peng Loh. "Transition metal-catalyzed cross-coupling reactions using organoindium reagents." Chemical Society Reviews 46, no. 3 (2017): 586–602. http://dx.doi.org/10.1039/c6cs00465b.

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This review highlights the versatility and significance of transition metal-catalyzed cross-coupling reactions employing mild and unique organoindium reagents with exceptional functional group compatibility and sometimes remarkable chemo- and stereoselectivities.
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5

Schumann, Herbert, Reza Mohtachemi, and Michael Schwichtenberg. "Synthese und Eigenschaften einiger neuer Organoindium-Methylenstannyl-Verbindungen / Preparation and Properties of Some New Organoindium Methylenestannyl Compounds." Zeitschrift für Naturforschung B 43, no. 11 (November 1, 1988): 1510–13. http://dx.doi.org/10.1515/znb-1988-1119.

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Abstract Me2Sn(CH2Li)2 reacts with Me2InCl or (Me2NCH2CH2O)2 InCl with formation of the new compounds Me2Sn(CH2InMe2)2 or Me2Sn(CH2In(OCH2CH2NMe2)2)2 . The compounds are characterized by elemental analyses, 1H, 13C, 119Sn NMR and IR spectra.
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6

Fischer, Roland A., Harald Sussek, Alexander Miehr, Hans Pritzkow, and Eberhard Herdtweck. "Organoindium azides: new precursors to indium nitride." Journal of Organometallic Chemistry 548, no. 1 (December 1997): 73–82. http://dx.doi.org/10.1016/s0022-328x(97)00333-1.

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7

SCHUMANN, H., TH D. SEUSS, and H. HEMLING. "ChemInform Abstract: Homoleptic Intramolecularly Stabilized Organoindium Compounds." ChemInform 24, no. 13 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199313243.

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8

Soulière, V., P. Abraham, M. Sacilotti, M. P. Berthet, J. Bouix, Y. Monteil, A. M. Pougnet, R. Mellet, A. Ougazzaden, and A. Mircéa. "A new organoindium precursor for electronic materials." Materials Science and Engineering: B 17, no. 1-3 (February 1993): 34–40. http://dx.doi.org/10.1016/0921-5107(93)90078-2.

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9

Merzweiler, Kurt, Ludwig Brands, and Jürgen Spohn. "Neue In2P2-Vierringe. Synthese und Kristallstrukturen von [{iPrIn(μ-tBu2P)Cl}2] und [{Me3SiCH2In(μ-tBu2P)Cl}2] / New Four-Membered In2P2 Rings. Snythesis and Crystal Structures of [{iPrIn(μ-tBu2P)Cl}2] and [{Me3SiCH2In(μ-tBu2P)Cl}2]." Zeitschrift für Naturforschung B 48, no. 10 (October 1, 1993): 1315–20. http://dx.doi.org/10.1515/znb-1993-1002.

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The reaction of organoindium halides RInCl2 with tBu2PSiMe3 leads to compounds of the type [{RIn(μ-tBu2P)Cl}2] (R = iPr: 1, Me3SiCH2: 2). According to the crystal structure determinations 1 and 2 contain planar In2P2 rings. The In atoms are coordinated to two bridging tBu2P groups, a terminal alkyl group and a terminal Cl atom
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10

Sestelo, J., R. Riveiros, D. Rodríguez, and L. Sarandeses. "Cross-Coupling of Organoindium Reagents with Propargylic Esters." Synfacts 2006, no. 6 (June 2006): 0594. http://dx.doi.org/10.1055/s-2006-934522.

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11

Yearwood, Burl, Shahid Ul Ghazi, Mary Jane Heeg, Nicholas Richardson, and John P. Oliver. "Organoindium Thiolate Oligomers: An X-ray Structural Study." Organometallics 19, no. 5 (March 2000): 865–71. http://dx.doi.org/10.1021/om990887b.

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12

Cintas, Pedro. "Synthetic Organoindium Chemistry: What Makes Indium so Appealing?" Synlett 1995, no. 11 (November 1995): 1087–96. http://dx.doi.org/10.1055/s-1995-5192.

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13

Beachley, O. T., Sun Hua L. Chao, Melvyn Rowen Churchill, and Charles H. Lake. "Use of organoindium hydrides for the preparation of organoindium phosphides. Synthesis and molecular structure of [(Me3CCH2)2InP(t-Bu)2]2." Organometallics 12, no. 10 (October 1993): 3992–97. http://dx.doi.org/10.1021/om00034a035.

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14

Shen, Zhi-Liang, Shun-Yi Wang, Yew-Keong Chok, Yun-He Xu, and Teck-Peng Loh. "Organoindium Reagents: The Preparation and Application in Organic Synthesis." Chemical Reviews 113, no. 1 (October 31, 2012): 271–401. http://dx.doi.org/10.1021/cr300051y.

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15

Liang, Yucang, and Martin Meixner. "Organoindium-modified monodisperse ellipsoid-/platelet-like periodic mesoporous silicas." Dalton Transactions 46, no. 23 (2017): 7495–505. http://dx.doi.org/10.1039/c7dt01132f.

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Indium-modified mondisperse ellipsoid-/platelet-like large-pore periodic mesoporous silica nanoparticles (MMSNs) SBA-15 have been prepared via molecular grafting of In[N(SiMe3)2]3. Surface ligand exchange led to the formation of heteroleptic In species, and the resulting surface In species were converted into crystalline In2O3 nanoparticles by calcination.
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16

FISCHER, R. A., H. SUSSEK, A. MIEHR, H. PRITZKOW, and E. HERDTWECK. "ChemInform Abstract: Organoindium Azides: New Precursors to Indium Nitride." ChemInform 29, no. 15 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199815189.

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17

Arndtsen, B., and D. Black. "Cu-Promoted Coupling of Imines, Acid Chlorides and Organoindium Reagents." Synfacts 2006, no. 7 (June 2006): 0712. http://dx.doi.org/10.1055/s-2006-941884.

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18

Uhl, Werner, and Barun Jana. "Bridging and Terminal Arrangement of Alkylperoxo Groups in Organoindium Peroxides." European Journal of Inorganic Chemistry 2009, no. 26 (September 2009): 3942–47. http://dx.doi.org/10.1002/ejic.200900449.

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19

CINTAS, P. "ChemInform Abstract: Synthetic Organoindium Chemistry: What Makes Indium so Appealing?" ChemInform 27, no. 16 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199616311.

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20

Grafova, Irina A., Sergei A. Khainakov, Vladimir V. Strelko, and Giovanni A. Battiston. "Organoindium Precursor Purification by New Sorbents Based on Titanium and Zirconium Phosphates." Adsorption Science & Technology 15, no. 6 (June 1997): 429–35. http://dx.doi.org/10.1177/026361749701500603.

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High purity requirements for organometallic precursors have recently become critical in the field of III–V semiconductor films obtained by chemical vapour deposition techniques. Traditional purification routes employing physical methods need to be replaced by ones which are more rapid and effective. Such a route is described in this paper. This involves the elimination of any traces of impurity by applying several combinations of sorbents. In this way, complete elimination of lithium impurities introduced during precursor synthesis has been achieved by the use of titanium or zirconium phosphate sorbents (usually used as acidic ion exchangers in aqueous media). The method also preserves the stability of the organoindium precursor which is normally extremely sensitive to moisture. A possible explanation for these observations is given.
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21

Uhl, Werner, Fritjof Schmock, and Wolfgang Petz. "The NaCl Adduct of the Iron-Indium Compound Fe2(CO)6(μ-CO)(μ-InR)2 [R = C(SiMe3)3] – a One-Dimensional Coordination Polymer with Sodium Oxygen Bridges." Zeitschrift für Naturforschung B 58, no. 5 (May 1, 2003): 385–88. http://dx.doi.org/10.1515/znb-2003-0505.

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The organoindium subhalide [R(Cl)In-In(Cl)R]2 [R = C(SiMe3)3] 1 reacts with Na2[Fe2(CO)8] to form an iron-indium coordination compound which was isolated as the sodium choride adduct [Na(THF)4][Fe2(CO)6(μ-CO)(μ-InR)2Cl] 2. The iron atoms of 2 are bridged by a CO ligand and two InR groups, the indium atoms of which are further connected by the μ2-bridging chlorine atom. Four THF molecules and two oxygen atoms of terminal CO ligands of different anions span the coordination sphere of the sodium cations to give a one-dimensional coordination polymer in the solid state.
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22

Jess, Kristof, Erin M. Hanada, Hannah Peacock, and Suzanne A. Blum. "Origins of Batch-to-Batch Variation: Organoindium Reagents from Indium Metal." Organometallics 39, no. 14 (July 14, 2020): 2575–79. http://dx.doi.org/10.1021/acs.organomet.0c00417.

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23

Self, Mark F., Andrew T. McPhail, and Richard L. Wells. "X-RAY CRYSTAL STRUCTURE OF AN ORGANOINDIUM ALKOXIDE DIMER, (Ph2InOSiMe3)2." Journal of Coordination Chemistry 29, no. 1-2 (June 1993): 27–32. http://dx.doi.org/10.1080/00958979308037122.

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24

Shen, Zhi-Liang, Shun-Yi Wang, Yew-Keong Chok, Yun-He Xu, and Teck-Peng Loh. "ChemInform Abstract: Organoindium Reagents: The Preparation and Application in Organic Synthesis." ChemInform 44, no. 12 (March 14, 2013): no. http://dx.doi.org/10.1002/chin.201312232.

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25

Schumann, Herbert, Uwe Hartmann, and Wilfried Wassermann. "Novel intramolecularly stabilized organogallium and organoindium compounds and their use in MOVPE." Polyhedron 9, no. 2-3 (January 1990): 353–60. http://dx.doi.org/10.1016/s0277-5387(00)80590-2.

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26

Nomura, Ryoki, Shin'ji Inazawa, Haruo Matsuda, and Shuji Saeki. "Thermal decomposition of organoindium compounds and preparation of indium-tin-oxide films." Polyhedron 6, no. 3 (January 1987): 507–12. http://dx.doi.org/10.1016/s0277-5387(00)81016-5.

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27

Schmidt, Bernd, Nastja Riemer, Christin Coswig, and Mike Shipman. "Palladium-Catalyzed Cross-Coupling of Arenediazonium Salts with Organoindium or Organobismuth Reagents." Synlett 29, no. 18 (October 11, 2018): 2427–31. http://dx.doi.org/10.1055/s-0037-1611001.

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28

Reetz, Manfred T., and Helmut Haning. "Ligand effects in selective addition reactions of organoindium reagents with carbonyl compounds." Journal of Organometallic Chemistry 541, no. 1-2 (August 1997): 117–20. http://dx.doi.org/10.1016/s0022-328x(97)00021-1.

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29

Beveridge, Ramsay E., Daniel A. Black, and Bruce A. Arndtsen. "Copper-Catalyzed Multicomponent Coupling of Organoindium Reagents with Nitrogen-Containing Aromatic Heterocycles." European Journal of Organic Chemistry 2010, no. 19 (May 14, 2010): 3650–56. http://dx.doi.org/10.1002/ejoc.201000231.

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30

Lee, Kooyeon, Hyunseok Kim, Juntae Mo, and Phil Ho Lee. "Palladium-Catalyzed Allyl Cross-Coupling Reactions with In Situ Generated Organoindium Reagents." Chemistry - An Asian Journal 6, no. 8 (May 2, 2011): 2147–57. http://dx.doi.org/10.1002/asia.201000890.

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31

Araki, Shuki, Tomoaki Horie, Motoshi Kato, Tsunehisa Hirashita, Hatsuo Yamamura, and Masao Kawai. "Regioselective allylation and alkylation of electron-deficient alkenes with organogallium and organoindium reagents." Tetrahedron Letters 40, no. 12 (March 1999): 2331–34. http://dx.doi.org/10.1016/s0040-4039(99)00179-3.

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32

Soengas, Raquel G., and Amalia M. Estévez. "Indium-mediated reaction of nitroethane and aldehydes: characterization of the nucleophilic organoindium species." Tetrahedron Letters 53, no. 5 (February 2012): 570–74. http://dx.doi.org/10.1016/j.tetlet.2011.11.094.

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33

Black, Daniel A., and Bruce A. Arndtsen. "General Approach to the Coupling of Organoindium Reagents with Imines via Copper Catalysis." Organic Letters 8, no. 10 (May 2006): 1991–93. http://dx.doi.org/10.1021/ol060277p.

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34

Lee, Phil Ho, Dong Seomoon, and Kooyeon Lee. "ChemInform Abstract: A Convenient Allylation of 1,n-Dicarbonyl Compounds Using Organoindium Reagents." ChemInform 33, no. 28 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200228117.

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35

Wu, Jie, Liang Zhang, and Yong Luo. "Transition-Metal-Catalyzed Cross-Couplings of Aryl Tosylates or Mesylates with Organoindium Reagents." Synlett 2010, no. 12 (June 30, 2010): 1845–48. http://dx.doi.org/10.1055/s-0030-1258116.

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36

Thorn, David L. "Transition metal-organoindium chemistry. Reaction of trialkylindium compounds with (cyclopentadienyl)(tricarbonyl)metal radicals." Journal of Organometallic Chemistry 405, no. 2 (March 1991): 161–71. http://dx.doi.org/10.1016/0022-328x(91)86268-u.

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37

Leigh, G. J. "Gmelin handbook of inorganic and organometallic chemistry, 8th edition, in organoindium compounds 1." Journal of Organometallic Chemistry 453, no. 1 (June 1993): C7—C8. http://dx.doi.org/10.1016/0022-328x(93)80346-d.

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38

Araki, Shuki, Tsunehisa Hirashita, Ken Shimizu, Takahiro Ikeda, and Yasuo Butsugan. "Reaction of α-halo organoindium reagents with carbonyl compounds and electron-deficient alkenes." Tetrahedron 52, no. 8 (February 1996): 2803–16. http://dx.doi.org/10.1016/0040-4020(96)00002-6.

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39

Hirashita, Tsunehisa, Ayumi Hayashi, Makoto Tsuji, Jiro Tanaka, and Shuki Araki. "Radical reactions initiated by the photochemical cleavage of carbon–indium bonds of organoindium compounds." Tetrahedron 64, no. 11 (March 2008): 2642–50. http://dx.doi.org/10.1016/j.tet.2008.01.013.

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40

Wieber, Markus, and Torsten Clarius. "SYNTHESE UND EIGENSCHAFTEN VON ORGANOGALLIUM(III)- UND ORGANOINDIUM(III)- VERBINDUNGEN MIT (O,O′)- DIORGANODITHIOPHOSPHATLIGANDEN." Phosphorus, Sulfur, and Silicon and the Related Elements 102, no. 1-4 (May 1995): 261–64. http://dx.doi.org/10.1080/10426509508042565.

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41

REETZ, M. T., and H. HANING. "ChemInform Abstract: Ligand Effects in Selective Addition Reactions of Organoindium Reagents with Carbonyl Compounds." ChemInform 29, no. 6 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199806086.

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42

Beveridge, Ramsay E., Daniel A. Black, and Bruce A. Arndtsen. "ChemInform Abstract: Copper-Catalyzed Multicomponent Coupling of Organoindium Reagents with Nitrogen-Containing Aromatic Heterocycles." ChemInform 41, no. 43 (September 30, 2010): no. http://dx.doi.org/10.1002/chin.201043046.

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43

Herbrich, Thomas, Karl-Heinz Thiele, and Kurt Merzweiler. "Die 3-(N,N-Dimethylamino)prop-1-enyl-Gruppe als Chelatligand in Organoindium-Verbindungen." Zeitschrift f�r anorganische und allgemeine Chemie 623, no. 10 (October 1997): 1679–83. http://dx.doi.org/10.1002/zaac.19976231033.

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44

Eaborn, C. "Gmelin handbook of inorganic and organometallic chemistry, 8th edition, in organoindium compounds, part 1." Journal of Organometallic Chemistry 464, no. 1 (January 1994): C36—C37. http://dx.doi.org/10.1016/0022-328x(94)87034-9.

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45

Jain, V. K., A. Wadawale, N. P. Kushwah, and M. K. Pal. "Synthesis, structures and utility of organogallium and organoindium complexes with oxo and thio ligands." Russian Chemical Bulletin 63, no. 4 (April 2014): 781–87. http://dx.doi.org/10.1007/s11172-014-0511-0.

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46

Tian, Xin, Michael Hagemann, Roland Fröhlich, Tania Pape, and Norbert W. Mitzel. "Preparation of Geminal Donor-Acceptor Units by Reactions of Low Valent Metal Halides with Iminium Chlorides." Zeitschrift für Naturforschung B 61, no. 2 (February 1, 2006): 170–78. http://dx.doi.org/10.1515/znb-2006-0209.

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AbstractThe organogallium compound [{Me2NCH2Ga(Cl,I)2}2] (1) and the organoindium compounds [Me2NCH2In(Cl,Br)2]2 (2) and [Me2NCH2InCl2]2 (3) have been prepared by the reactions of the low valent metal halides “GaI”, InBr and InCl with the iminium salt [Me2N=CH2]Cl. Compounds 1 and 2 are heterohalogen mixtures. These compounds were characterised by NMR spectroscopy and mass spectrometry, 1 furthermore by single crystal X-ray diffraction and 3 by elemental analysis. During the work-up procedure, minor amounts of hydrogen halide adducts of compounds 2 and 3 were isolated as single crystals, which contain a further equivalent of THF. These zwitter-ionic species Me2N(H)CH2In(Br,Cl)3·THF (2·H(Cl,Br)·THF) and Me2N(H)CH2InCl3 ·THF (3 ·HCl ·THF) were identified by single crystal X-ray diffraction. Methylation reactions of compounds 1 and 2 with MeLi gave two well-established compounds [{Me2NCH2GaMe2}2] and [{Me2NCH2InMe2}2], which were obtained previously by different preparation procedures.
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47

Nomura, Ryoki, Satoru Fujii, Kouichi Kanaya, and Haruo Matsuda. "Oxygen- or sulphur-containing organoindium compounds for precursors of indium oxide and sulphide thin films." Polyhedron 9, no. 2-3 (January 1990): 361–66. http://dx.doi.org/10.1016/s0277-5387(00)80591-4.

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48

Zhang, Liang, Yong Luo, and Jie Wu. "ChemInform Abstract: Transition Metal Catalyzed Cross-Couplings of Aryl Tosylates or Mesylates with Organoindium Reagents." ChemInform 41, no. 48 (November 4, 2010): no. http://dx.doi.org/10.1002/chin.201048077.

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49

Araki, Shuki, Tomoaki Horie, Motoshi Kato, Tsunehisa Hirashita, Hatsuo Yamamura, and Masao Kawai. "ChemInform Abstract: Regioselective Allylation and Alkylation of Electron-Deficient Alkenes with Organogallium and Organoindium Reagents." ChemInform 30, no. 25 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.199925070.

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50

Hepp, Aloysius F., Maria T. Andras, Sheila G. Bailey, and Stan A. Duraj. "Room temperature synthesis of copper indium diselenide in non-aqueous solution using an organoindium reagent." Advanced Materials for Optics and Electronics 1, no. 2 (April 1992): 99–103. http://dx.doi.org/10.1002/amo.860010207.

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