Indium-mediated atom-transfer cyclizations and reductive cyclizations

Yanada, Reiko; Nishimori, Nobuaki; Matsumura, Akira; Fujii, Nobutaka; Takemoto, Yoshiji

doi:10.1016/s0040-4039(02)00880-8

Cited by 43 publications

(14 citation statements)

References 33 publications

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“…15a,b A low-valent indium species, prepared in situ from indium powder, can be employed in either ATRCs or reductive radical cyclisations of iodoalkynes (Scheme 20). 96,97 Treatment of iodide 61 with 1 equiv of indium and 0.5 equiv of iodine gives the alkenyl iodide 62 in good yield. The reaction permits the synthesis of a range of mono-and bi-cyclic heterocycles.…”

Section: Indium Metal-based Reagentsmentioning

confidence: 99%

Radicals in organic synthesis. Part 1

Rowlands

2009

Tetrahedron

202

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Section: Indium Metal-based Reagentsmentioning

confidence: 99%

Radicals in organic synthesis. Part 1

Rowlands

2009

Tetrahedron

202

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“…[11] Although the cyclization product (E)-6a was obtained exclusively, the chemical yield of 6a was only 40% due to the recovery of the starting material 4a in 45% yield (Table 1, run 1). After optimization of the reaction conditions, we found that additives had a dramatic effect on the reaction rate.…”

Section: In-mediated Radical Cyclization Of 2-iodoynamidesmentioning

confidence: 99%

Stereoselective Synthesis of 3‐Alkylideneoxindoles using Tandem Indium‐Mediated Carbometallation and Palladium‐Catalyzed Cross‐Coupling Reactions

et al. 2005

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The first efficient methods for the stereoselective synthesis of various (E)-, (Z)-, and disubstituted 3-alkylideneoxindoles via radical cyclization reactions were investigated using tandem indium-mediated carbometallation and palladium-catalyzed crosscoupling reactions. The proper combination of substrates and reaction conditions is important for good yields. The key step is the first stereoselective carboindation reaction using the strong coordination ability of an indium cation to the amide carbonyl oxygen. We applied this method to the synthesis of TMC-95A precursor. A new N-debenzylation method with N-hydroxyphthalimide-O 2 -Co(OAc) 2 -Mn(OAc) 2 was also developed using a one-electron oxidation procedure.

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“…heterocyclic alkenes (277) and (278) [83,84] -the synthons for various HIV-protease inhibitors have been obtained (Scheme 90). The indium-mediated intramolecular cascade free radical additions have been used for synthesis of heterocycles.…”

Section: Intramolecular Cyclizationsmentioning

confidence: 99%

Indium Reagents in Heterocyclic Chemistry

Kumar

Kaur²,

Kumar

2005

COC

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Indium due to its moderate heterophilicity and recyclability plays significant role in indium catalyzed / mediated reactions of heterocycles. The co-ordination of hetero atom of the heterocycle with indium and the electronic contributions of heteroatoms in the ring provide more versatility in comparison to acyclic and carbocyclic systems. Here, the applications of indium reagents in heterocyclic chemistry have been reviewed. The review discusses the applications of indium salts -both inorganic and organometallics in the transformations of three, four, five and six membered heterocycles; synthesis of heterocycles through cycloaddition, cyclocondensation reactions, intramolecular cyclization, cascade reaction and heterocyclic modifications on the ring or on the appendage etc.

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Indium-mediated atom-transfer cyclizations and reductive cyclizations

Cited by 43 publications

References 33 publications

Radicals in organic synthesis. Part 1

Radicals in organic synthesis. Part 1

Stereoselective Synthesis of 3‐Alkylideneoxindoles using Tandem Indium‐Mediated Carbometallation and Palladium‐Catalyzed Cross‐Coupling Reactions

Indium Reagents in Heterocyclic Chemistry

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