A facile preparation of indium enolates and their Reformatsky- and Darzens-type reactions

Hirashita, T.; Kinoshita, Kenji; Yamamura, Hisao; Kawai, Maki; Araki, Shuki

doi:10.1039/a907334e

Cited by 40 publications

(8 citation statements)

References 18 publications

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“…This would lead to the corresponding [ClFe III CH(CH 3 )CO 2 CH 3 ]. By analogy with the numerous Reformatsky reactions performed in the presence of zinc, chromium or indium, etc., we may then envisage the formation of an enolate followed by the reaction with the ketone leading to an iron-alkoxide [31,32]. The latter is then easily converted into the corresponding b-hydroxyester by hydrolysis with 2M HCl.…”

Section: Study Of Febr 2 In the Presence Of 22 0 -Bipyridine Methylmentioning

confidence: 99%

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Mechanistic investigation of the iron-mediated electrochemical formation of β-hydroxyesters from α-haloesters and carbonyl compounds

Buriez

Durandetti

Périchon

2005

Journal of Electroanalytical Chemistry

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Section: Study Of Febr 2 In the Presence Of 22 0 -Bipyridine Methylmentioning

confidence: 99%

“…Since the reaction is initiated by insertion of zinc into the halogen-carbon bond, most efforts have been focused on the activation of zinc [5][6][7][8][9]. Nevertheless, in the past decade, replacement of zinc with another metal such as chromium [10], indium [11,12], or manganese [13,14] has been attracting increased attention.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic investigation of the iron-mediated electrochemical formation of β-hydroxyesters from α-haloesters and carbonyl compounds

Buriez

Durandetti

Périchon

2005

Journal of Electroanalytical Chemistry

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“…Thus, indium and its compounds have worked as reagents as well as catalysts in some carbon-carbon bondforming reactions, such as allylation of carbonyl compounds [2], Reformatsky reactions [3], aldol reactions [4], Diels-Alder reactions [5], Michael reactions [6], Friedel-Crafts reactions [7], and reductive coupling reactions [8]. In the cases of catalytic reactions, however, a rather large amount of indium salts (10-20 mol %) has normally been employed.…”

Section: Introductionmentioning

confidence: 99%

Indium‐catalyzed reductive coupling of aromatic carbonyl compounds and imines in the presence of aluminum and chlorosilanes

Ohtaka

Mori

Uemura

2001

Heteroatom Chemistry

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Reductive homocoupling of aromatic aldehydes, ketones, and imines has been achieved in tetrahydrofuran (THF) at room temperature using a catalytic amount of InCl 3 (0.5-3.0 mol %) under a nitrogen atmosphere in the presence of chlorotrimethylsilane (TMSCl) and aluminum metal (Al) to provide the corresponding 1,2-diols and 1,2-diamines, respectively, in good to moderate yields. Other indium compounds such as In(NO 3 ) 3 , cyclopentadienylindium, and indium metal have also been revealed to be effective as catalysts. The catalytic effect of the indium compound is remarkable, and, thus, without it, no reaction occurs in the case of aromatic aldehydes and aldimines, and an induction period is quite long in the case of aromatic ketones. Without either TMSCl or Al, no reaction proceeds even in the presence of the catalyst. Unfortunately, the diastereoselectivity of the products (dl and meso) is not high. Although the precise reaction scheme is not yet clear, we tentatively propose that a redox-active In-Al alloy might be formed on the surface of aluminum in the presence of TMSCl, and an electron transfer from the alloy to substrate might White solid; 1 H NMR [CDCl 3 ‫ם‬ D 2 O (few drops), 400 MHz] d ‫ס‬ 1.64 [1.81] (6H, s), 6.17-7.56 (20H, m); 13 C NMR [CDCl 3 ‫ם‬ D 2 O (few drops), 75.5 MHz] d ‫ס‬

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“…New CÀ C bonds are formed in the coupling reactions and have been recognized as potential tools in the field of organic synthesis. Indium(III) chloride has been employed for the different coupling reactions such as Reformatsky and Darzenstype reactions, [79] Aldol reactions [80] and Diels-Alder reactions. [81] In 2020, Pinet et.…”

Section: Coupling Reactionsmentioning

confidence: 99%

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

Datta

2021

ChemistrySelect

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This review summarizes recent advances of indium trichloride catalyzed synthesis of different organic compounds. It is obvious that InCl3 co‐ordinates with C−C and/or C‐heteroatom multiple bonds and thereby makes them very prone to nucleophilic attack to form a new bond. This Lewis acid catalyst also activates oxiranes to produce aldehydes. Multicomponent synthesis including C−C bond formation reaction and construction of N, O and S‐containing heterocycles are discussed in organic solvents as well as in water. This article highlights recent developments and application of indium(III) chloride as a catalyst in organic synthesis from 2015 to 2020. The mechanism of few important reactions is discussed in detail which will be very useful for the readers.

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A facile preparation of indium enolates and their Reformatsky- and Darzens-type reactions

Cited by 40 publications

References 18 publications

Mechanistic investigation of the iron-mediated electrochemical formation of β-hydroxyesters from α-haloesters and carbonyl compounds

Mechanistic investigation of the iron-mediated electrochemical formation of β-hydroxyesters from α-haloesters and carbonyl compounds

Indium‐catalyzed reductive coupling of aromatic carbonyl compounds and imines in the presence of aluminum and chlorosilanes

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

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