Chloride indium

Indium chloride in polar solvents such as acetone or acetonitrile leads to good diastereoselectivity with cyclohexanecarboxaldehyde and other representative aldehydes.176... 

The indium-mediated allylation carried out with allylstannanes in combination with indium chloride in aqueous medium was reported by Marshall et al.113 Allylindium was proposed as the reaction intermediate. Various aldehydes can be alkylated very efficiently with 3-bromo-2-chloro-l-propene mediated by indium in water at room temperature. Subsequent treatment of the compound with ozone in methanol followed by workup with sodium sulfite provided the desired hydroxyl ester in high yield.114... 

An indium chloride-catalyzed coupling of alkynes to aldehydes was also possible in giving a, (J>-unsaturatcd carbonyl compounds in water in low yields (Eq. 8.88).223 (Alkynylation is discussed in Chapter 4 on alkynes.)... 

By reacting aniline with 2,3-dihydrofuran or dihydropyran and a catalytic amount of Lewis acid such as indium chloride in water, various tetrahydroquinoline derivatives were obtained by Li via an in-situ hetero-Diels-Alder reaction.130 Alternatively, similar compounds... 

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... 

Diels-Alder reactions are one of the most famous examples which are accderated by a Lewis acid. Various water-stable Lewis adds such as Ln(OTf)3,1371 methylrhenium trioxide,1381 copper nitrate,1391 copper bis(dodecyl sulfate) (4b),1401 indium chloride,1411 and bismuth triflate1421 have been used for Diels-Alder and aza-Diels-Alder reactions in water. Furthermore, a catalytic asymmetric Dids-Alder reaction in water using a copper complex of an amino... 

Furthermore, the use of a Lewis acid promoter leads to increased stereoselectivities (Table 19, entry C)252,254. Compared to the aprotic reaction, where allyl silane was used instead of allyl bromide and indium chloride, an almost complete reversal of the diastereos-electivity was found. It was demonstrated recently that the Lewis acid catalysed allylation reaction can be carried out efficiently without any organic solvent in saturated ammonium chloride solution255. Finally, Lewis acid catalysed Mannich reactions can be carried out conveniently in mixtures of organic solvents and water. However, the exact role of the Lewis acid catalyst has not been clarified (Table 19, entry D)253. The same reaction can be carried out in pure water with catalysis by indium trichloride256. 

Indium chloride inorg chem InClj Hygroscopic white powder, soluble in water and alcohol. in-de-om kl6r,Td ... 

Woods JS, Carver GT, Fowler BA Altered regulations of hepatic heme metabolism by indium chloride. Toxicol Appl Pharmacol 49 455 61, 1979... 

Renz 4 describes an additive compound of indium trichloride and pyridine, tripyridino-indium trichloride, [In(C5H5N)3]Cl3, which is prepared by adding pyridine to a solution of indium trichloride in alcohol. After standing for a short time, small needle-shaped crystals separate of melting-point 253° C. The compound is not hygroscopic like indium chloride, is somewhat sparingly soluble in alcohol, and is insoluble in ether. It decomposes on warming with water with formation of indium hydroxide, In(OH)3. Aluminium trichloride and iron trichloride form similar addition products. 

Ammino-derivatives of Indium Chloride and Thallio Bromide. 

Indium Metavanadate, In(V03)3.2H20, is a yellow substance produced by the action of sodium metavanadate on indium chloride solution.12... 

In [210, 211] the solid-phase reaction of unsaturated ketones and anilines on a surface of silica gel in the presence of indium chloride under microwave irradiation was described. The library consists of 15 quinolines in yields of 55-87% which were generated quickly and characterized. Ranu et al. [211] showed that dihydro derivatives of qiunolines (e.g., 270 and 273) can also be synthesized, but in this case one component of the reaction must be a 4,4-disubstituted methyl vinyl ketone, for example, mesityl oxide 52 or l-(2-methylcyclopent-l-enyl)ethanone 272 (Scheme 3.75). 

Binary regiocontrolled pentadienylation of imines with a pentadienyltin reagent has been achieved. While A-phenylimines affords e-adducts (1,3-dienes) exclusively under Lewis-acidic conditions, the combination of A-tosylimines and indium chloride or zinc chloride as a Lewis acid gives y-adducts (1,4-dienes) preferentially (Scheme 65).266... 

Figure 16. Reaction pathways for Se2 addition of enantioenriched y-OMOM allylic indium chlorides to aldehydes.

Additions of the transient y-OMOM crotyl indium chloride reagents to a-oxyge-nated aldehydes are strongly reagent-controlled. Thus the (R) and (S) reagents add to protected threose and erythrose aldehydes with high diastereoselectivity (Eq. 59) [75]. These additions are complementary to those previously effected with the y-BusSn counterparts (Eq. 45). It is thus possible to prepare precursors to the eight diastereomeric hexoses and their enantiomers from threose- and erythrose-derived aldehydes and their enantiomers plus the a-OMOM crotyl tributylstannane enantiomers. 

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