Indium metal reactions with

There are no reports of well-characterized InH2 or its adducts. However, the indium(II) hydride species HInNH2 and HInPH2 have been generated by thermal and photoactivated reactions of indium metal atoms with NH3 or PH3 in solid argon matrices. They have been identified by their IR spectra. 

The indium-mediated Barbier reaction has certainly become one of the most popular reactions for creating a carbon-carbon bond under aqueous conditions and has led to spectacular developments in recent years. Compared to other metals, indium is resistant to oxidation, hydrolysis, and has a very low first ionization potential (5.79 eV, in contrast to the second one which is quite normal) which confers on it a remarkable reactivity in Barbier-type reactions. In 1991, Li and co-workers reported the first allylation of aldehydes and ketones mediated by indium in water without any additives or special activation [133]. In particular, the use of indium allowed reactions with acid-sensitive compounds [134] or the preparation of complex carbohydrates such as deaminated... 

Sulfates. Indium metal and its oxides dissolve in warm sulfuric acid to give a solution of the trisulfate [13464-82-9], In2(S0 2- It is a white, crystalline, deUquescent soHd, readily soluble in water that forms double salts with alkaLi sulfates and some organic substituted ammonium bases. Concentration of the acidified trisulfate solution produces indium acid sulfate crystal [57344-73-7], In(HS0 2> other reaction conditions give basic sulfates. 

Metallic Antimonides. Numerous binary compounds of antimony with metallic elements are known. The most important of these are indium antimonide [1312-41 -0] InSb, gallium antimonide [12064-03-8] GaSb, and aluminum antimonide [25152-52-7] AlSb, which find extensive use as semiconductors. The alkali metal antimonides, such as lithium antimonide [12057-30-6] and sodium antimonide [12058-86-5] do not consist of simple ions. Rather, there is appreciable covalent bonding between the alkali metal and the Sb as well as between pairs of Na atoms. These compounds are useful for the preparation of organoantimony compounds, such as trimethylstibine [594-10-5] (CH2)2Sb, by reaction with an organohalogen compound. 

The chemistry of indium metal is the subject of current investigation, especially since the reactions induced by it can be performed in aqueous solution.15 The selective reductions of ethyl 4-nitrobenzoate (entry 1), 2-nitrobenzyl alcohol (entry 2), l-bromo-4-nitrobenzene (entry 3), 4-nitrocinnamyl alcohol (entry 4), 4-nitrobenzonitrile (entry 5), 4-nitrobenzamide (entry 6), 4-nitroanisole (entry 7), and 2-nitrofluorenone (entry 8) with indium metal in the presence of ammonium chloride using aqueous ethanol were performed and the corresponding amines were produced in good yield. These results indicate a useful selectivity in the reduction procedure. For example, ester, nitrile, bromo, amide, benzylic ketone, benzylic alcohol, aromatic ether, and unsaturated bonds remained unaffected during this transformation. Many of the previous methods produce a mixture of compounds. Other metals like zinc, tin, and iron usually require acid-catalysts for the activation process, with resultant problems of waste disposal. 

Although not formally the enamine synthesis, reaction of an enamine with methyl hromoacetate in the presence of indium metal leads to a-aUcylation R2N-CH=CHR R2N-CH(R )CHR. ... 

One notable result is the treatment of 2-hydroxy cyclic ether analog, 2-deoxy-D-ribose with aniline in water catalyzed by InCl3 to afford the novel tricyclic tetrahydroquinoline compounds (Eq. 12.60). The reaction can also be catalyzed by recoverable cation-exchange resin instead of indium chloride.132 By using a stoichiometric amount of indium metal, a domino reaction of nitroarenes with 2,3-dihydrofuran generates the same products. 133... 

As shown in Eq. 6.59, Rapoport has prepared sinefungin, nucleoside antibiotics, via nitro-aldol reaction, dehydration, and reduction with Zn in acetic add.115a [i-Nitrostyrenes are selectivity reduced to the corresponding oximes by indium metal in aqueous methanol under neutral conditions.11515... 

In this context, Yadav and coworkers have recently developed a mild and efficient procednre for the selective rednction of / -nitrostyrenes 22 to oximes 23 using indium metal in aqueous methanol under neutral reaction conditions (Scheme 19). Similarly, a-alkoxy oximes 24 are formed in good yields by the treatment of nitroolefins with metalhc indium and trimethylsilyl chloride in anhydrous methanol (Scheme 19). 

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