Indium I iodide

Reaction with Propargyl Halides. The indium-mediated coupling of propargyl bromide with a variety of imines and imine oxides afforded homo-propargylamine derivatives in aqueous media under mild conditions.78 Propargylation of glyoxylic oxime ether in the presence of a catalytic amount of palladium(O) complex and indium(I) iodide in aqueous media was also studied (Eq.11.47).79... 

Indium(I) iodide serves as a two electron reducing agent to promote a Ni-catalyzed allylation of benzaldehyde with 1,3-dienes [23]. In the presence of a catalytic amount of Ni(acac)2 and a stoichiometric amount of Ini, 1,3-butadiene reacts with 2 equiv. of benzaldehyde to provide a mixture of a 1,4-diol 28 and 1,6-diol 29 and/or with 1 equiv. of benzaldehyde to give 27 (Eq. 8). The product distribution of 27-29 markedly depends on the solvent, the ligand, and the additive employed (Table 2). The combination of Ni(acac)2, PPI13, and 3 equiv. of water in DMI provides the 1,4-diol 28 as the major product (run 1). Under similar conditions, dppb dramatically changed the reaction course and the mono-allylation product 27 is produced exclusively (run 2). In contrast to these, the reaction in dry THF provides the 1,6-diol 29 in excellent yield (rim 3). 

Methylenetetrahydrofurans can also be realized by an intramolecular radical cyclization of bromoalkynes utilizing indium(I) iodide as a radical initiator <06TL2859>. 3-Diiodomethylenetetrahydrofurans were also prepared from l,to-diiodo-l-alkynes in the presence of l-hexynyllithium<06CC638>. 

Indium (I) iodide Indium iodide (8) Indium iodide (Ini) (9) (13966-94-4)... 

SYNTHESIS AND UTILIZATION OF INDIUM (I) IODIDE FOR IN SITU FORMATION OF ENANTIOENRICHED ALLENYLINDIUM REAGENTS AND THEIR ADDITION TO ALDEHYDES (2R,3S,4S)-1-(tert-BUTYLDIPHENYLSILYLOXY)-2,4-DIMETHYL-5-HEXYN-3-OL [5-Hexyn-3-ol, 1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2,4-dimethyl-,... 

Indium(I) iodide has been shown to promote the cleavage of dialkyl disulfides, generating thiolate anions that then undergo facile addition to a -unsaturated ketones,... 

Allyl and benzyl bromides react with a,/ -unsaturated nitriles in the presence of indium(i) iodide under sonication to produce the corresponding allylated and benzylated imines, involving exclusive addition of the allyl/benzyl group to the nitrile moiety (Equation (63)).273 The reaction of allylindium reagents with methyl cyanoacetates affords the corresponding allylation-enamination products (Equation (64)).27 l-Acyl-l,2-dihydropyridines are prepared by indium-mediated allylation of 1-acylpyridinium salts (Equation (65)).275 Quinoline and isoquinoline activated by... 

The zinc-mediated Reformatsky reaction is one of the classical methods for carbon-carbon bond formation. To date, various main group metals and transition metals have been used for this reaction. Rieke s activated indium powder mediates readily the coupling of ethyl a-bromoacetate and a variety of carbonyl compounds yielding /3-hydroxy esters in good yields (Scheme 87).3 Later, commercially available indium powder has been found to be equally effective for the indium-based Reformatsky reaction in THF.28 This indium Reformatsky reaction is accelerated by ultrasound irradiation (Scheme 88).322,323 Indium(i) iodide also mediates the Reformatsky reaction of aldehydes and ketones to give /3-hydroxy esters, presumably via organoindium(m) diiodide (Scheme 89).27... 

Reaction of phenacyl iodide with indium metal gives 3,4-epoxy-1,3-diphenyl-1-butanone which, on treatment with silica gel, gives 2,4-diphenylfuran and 2,4-diphenyl-4-oxobutanal (Scheme 92). Metallic indium as well as indium(i) iodide mediate the aldol condensation between ce-halo ketone and aldehyde.333... 

In the past decade much effort in organoindium chemistry has been devoted to study of carbonyl allylation and aUylindation of carbon-carbon multiple bonds with allylic indium reagents. Apart from the conventional transmetalation of allyl-lifhium or aUyl Grignard reagents with indium(III) halides, a method widely used for preparation of allyhndium(III) compounds is the oxidative addition of metallic indium or indium(I) iodide to aUyhc substrates [3, 6]. Transmetalation of allylstan-nane with indium(III) chloride also gives allylindium(III) [7]. Allylindium(I) was recently prepared by transmetalation of allylmercury with metallic indium in water this compound is regarded as an intermediate in the allylation of carbonyl compounds in aqueous media [8]. A new method of preparation of allylic in-dium(III) reagents - reductive transmetalation of a 7r-allylpalladium(ll) complex with indium(I) salts has been reported this enables the use of a wide variety of allylic compounds and solvents [9]. 

AUylation and propargylation reactions. In the presence of the (Ph3P)4Pd catalyst, indium(I) iodide form organoindium(III) reagents with allylic halides and propargylic mesylates that react with carbonyl compounds in various solvents. 

Ini Indium(I) iodide, 7 19, 20 Inl2 Indium(II) iodide, 7 19, 20 [Ir(C2HsNH2)6Cl]a2 Chloro-pentakis (ethylamine)iridium-... 

Mercury(II) iodide Mercury(I) iodide Holmium Indium(I) iodide Potassium iodide Lithium iodide Sodium iodide Rubidium iodide Thallium(I) iodide Iodine... 

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