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Indium in Organic Synthesis
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Indium in Organic Synthesis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 May 2018) | Viewed by 34830

Special Issue Editors

Prof. Dr. Akio Baba

E-Mail Website
Guest Editor
Osaka University 2-8, Yamadaoka, Suita, Osaka 565-0871, Japan
Interests: organic synthesis; organometallic chemistry; indium chemistry; Lewis acids; organotin chemistry
Prof. Dr. Makoto Yasuda

E-Mail Website
Guest Editor
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
Interests: organic synthesis; organometallic chemistry; Lewis acids; coordination chemistry; metal complexes; organic structural chemistry

Special Issue Information

Dear Colleagues,

A variety of indium reagents has played an important role in fundamental organic transformations, since the first practical preparation of allylic indium species was demonstrated by Araki et al. in a 1988 report. In spite of a short amount of time since the beginning of indium chemistry, amazing diverse applications have been developed, such as Barbier-type reaction, reduction, Lewis acid-catalyzed addition, carbometalation, transition metal-catalyzed coupling, and radical reactions, in the last three decades. Either indium metal, indium(I) and indium(III) species have been smartly employed in those organic transformations. Almost all applications are strongly based on characteristic high functional group tolerance, even toward active protons, including water. Recently, indium chemistry has been presenting attractive synthetic procedures under the conditions where other reagents hardly show their activity. We are delighted to be Guest Editors of this Special Issue on “Indium in Organic Synthesis”. We believe that the moderate reactivity of indium reagents can be precisely activated to achieve desired selective reactions. We welcome a wide range of articles on indium chemistry.

Prof. Dr. Akio Baba
Prof. Dr. Makoto Yasuda
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Indium chemistry
  • Lewis acids
  • C-C bond formation
  • Oxidation and reduction
  • Aqueous media
  • Catalysis
  • Organoindium compounds
  • Indium hydride
  • Structure of organoindiums

Published Papers (8 papers)

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Research

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14 pages, 6416 KiB  
Communication
Regio- and Stereoselective Allylindation of Alkynes Using InBr3 and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes
by Yoshihiro Nishimoto, Junyi Yi, Tatsuaki Takata, Akio Baba and Makoto Yasuda
Molecules 2018, 23(8), 1884; https://doi.org/10.3390/molecules23081884 - 27 Jul 2018
Cited by 7 | Viewed by 4307
Abstract
Regioselective anti-allylindation of alkynes was achieved using InBr3 and allylic silanes. Various types of alkynes and allylic silanes were applicable to the present allylindation. This sequential process used the generated 1,4-dienylindiums to establish novel synthetic methods for skipped dienes. The 1,4-dienylindiums [...] Read more.
Regioselective anti-allylindation of alkynes was achieved using InBr3 and allylic silanes. Various types of alkynes and allylic silanes were applicable to the present allylindation. This sequential process used the generated 1,4-dienylindiums to establish novel synthetic methods for skipped dienes. The 1,4-dienylindiums were characterized by spectral analysis and treated with I2 to stereoselectively give 1-iodo-1,4-dienes. The Pd-catalyzed cross coupling of 1,4-dienylindium with iodobenzene successfully proceeded in a one-pot manner to afford the corresponding 1-aryl-1,4-diene. Full article
(This article belongs to the Special Issue Indium in Organic Synthesis)
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9 pages, 1592 KiB  
Communication
Indium-Mediated Allylation of Carbonyl Compounds in Ionic Liquids: Effect of Salts in Ionic Liquids
by Tsunehisa Hirashita, Fusako Takahashi, Takayuki Noda, Yuji Takagi and Shuki Araki
Molecules 2018, 23(7), 1696; https://doi.org/10.3390/molecules23071696 - 11 Jul 2018
Cited by 3 | Viewed by 3243
Abstract
The In-mediated allylation of carbonyl compounds can be performed in various types of solvents including ionic liquids. However, we have found that in [bmim][BF4] (where bmim = 1-butyl-3-methylimidazolium), the In-mediated coupling of crotyl bromide with benzaldehyde gives a complex mixture, and [...] Read more.
The In-mediated allylation of carbonyl compounds can be performed in various types of solvents including ionic liquids. However, we have found that in [bmim][BF4] (where bmim = 1-butyl-3-methylimidazolium), the In-mediated coupling of crotyl bromide with benzaldehyde gives a complex mixture, and some additives, such as halides and amines, are crucial for the successful conversion to the corresponding γ-adduct. Instead, the addition of alcohols or water promotes the formation of the α-adduct. An asymmetric induction with up to 62% enantiomeric excess (ee) was observed employing cinchonidine as an additive in a binary solvent consisting of an ionic liquid and dichloromethane. Full article
(This article belongs to the Special Issue Indium in Organic Synthesis)
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12 pages, 4195 KiB  
Article
Triorganoindium Reagents in Rh-Catalyzed C–H Activation/C–C Cross-Coupling Reactions of 2-Arylpyridines
by Ricardo Riveiros, Rubén Tato, José Pérez Sestelo and Luis A. Sarandeses
Molecules 2018, 23(7), 1582; https://doi.org/10.3390/molecules23071582 - 29 Jun 2018
Cited by 3 | Viewed by 3611
Abstract
The activation of C–H bonds through catalytic reactions using transition metals is an important challenge in organic chemistry in which the intermediates are related to those produced in the classical cross-coupling reactions. As part of our research program devoted to the development of [...] Read more.
The activation of C–H bonds through catalytic reactions using transition metals is an important challenge in organic chemistry in which the intermediates are related to those produced in the classical cross-coupling reactions. As part of our research program devoted to the development of metal-catalyzed reactions using indium organometallics, a protocol for the C–H activation and C–C coupling of 2-arylpyridines with triorganoindium reagents under Rh(I) catalysis is reported. Under the optimized conditions, we found that Me3In and Ar3In reagents reacted with 2-arylpyridines and related compounds in the presence of Rh(PPh3)3Cl, in PhCl/THF (9:1), at 120 °C for 48 h, to afford the ortho-coupling products in moderate to good yields. The nitrogen atom in the pyridine ring acts as a directing group to assist the functionalization at the ortho position of the aryl group forming a new C–C bond at this position. Full article
(This article belongs to the Special Issue Indium in Organic Synthesis)
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11 pages, 8791 KiB  
Article
Indium-Catalyzed Direct Conversion of Lactones into Thiolactones Using a Disilathiane as a Sulfur Source
by Yohei Ogiwara, Ken Takano, Shuhei Horikawa and Norio Sakai
Molecules 2018, 23(6), 1339; https://doi.org/10.3390/molecules23061339 - 02 Jun 2018
Cited by 6 | Viewed by 4136
Abstract
An indium-catalyzed reaction of lactones and a disilathiane leading to thiolactones is described. The direct synthesis of thiolactones from lactones with an appropriate sulfur source is one of the most attractive approaches in organic and pharmaceutical chemistry. In this context, we found an [...] Read more.
An indium-catalyzed reaction of lactones and a disilathiane leading to thiolactones is described. The direct synthesis of thiolactones from lactones with an appropriate sulfur source is one of the most attractive approaches in organic and pharmaceutical chemistry. In this context, we found an indium-catalyzed direct conversion of lactones into thiolactones in the presence of elemental sulfur and a hydrosilane via formation of the disilathiane in situ. On the basis of the previous reaction, the application utilizing the disilathiane as a sulfur source was performed herein for the efficient synthesis of a variety of thiolactone derivatives from lactones by an indium catalyst. Full article
(This article belongs to the Special Issue Indium in Organic Synthesis)
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11 pages, 1316 KiB  
Communication
In(III)-TMSBr-Catalyzed Cascade Reaction of Diarylalkynes with Acrylates for the Synthesis of Aryldihydronaphthalene Derivatives
by Qiu-Chi Zhang, Wen-Wei Zhang, Liang Shen, Zhi-Liang Shen and Teck-Peng Loh
Molecules 2018, 23(4), 979; https://doi.org/10.3390/molecules23040979 - 23 Apr 2018
Cited by 3 | Viewed by 5091
Abstract
A combined Lewis acid system comprising of two or more Lewis acids occasionally exhibits augmented catalytic activity in organic transformations which are otherwise unrealizable by either of the components exclusively. On the other hand, the efficient construction of multiple new C-C bonds and [...] Read more.
A combined Lewis acid system comprising of two or more Lewis acids occasionally exhibits augmented catalytic activity in organic transformations which are otherwise unrealizable by either of the components exclusively. On the other hand, the efficient construction of multiple new C-C bonds and polycyclic structures in minimal steps remains a subject of great interest in both academia and industry. Herein we report an efficient method to assemble aryldihydronaphthalene derivatives via a cascade reaction of diarylalkynes with acrylates under the catalysis of a combined Lewis acid derived from In(III) salt and TMSBr. Full article
(This article belongs to the Special Issue Indium in Organic Synthesis)
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18 pages, 1736 KiB  
Article
Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives
by Kyohei Yonekura, Mika Shinoda, Yuko Yonekura and Teruhisa Tsuchimoto
Molecules 2018, 23(4), 838; https://doi.org/10.3390/molecules23040838 - 05 Apr 2018
Cited by 22 | Viewed by 5456
Abstract
We disclose herein the first synthetic method that is capable of offering heteroaryl[b]quinolines (HA[b]Qs) with structural diversity, which include tricyclic and tetracyclic structures with (benzo)thienyl, (benzo)furanyl, and indolyl rings. The target HA[b]Q is addressed by the annulation [...] Read more.
We disclose herein the first synthetic method that is capable of offering heteroaryl[b]quinolines (HA[b]Qs) with structural diversity, which include tricyclic and tetracyclic structures with (benzo)thienyl, (benzo)furanyl, and indolyl rings. The target HA[b]Q is addressed by the annulation of o-acylanilines and MeO–heteroarenes with the aid of an indium Lewis acid that effectively works to make two different types of the N–C and C–C bonds in one batch. A series of indolo[3,2-b]quinolines prepared here can be subsequently transformed to structurally unprecedented cryptolepine derivatives. Mechanistic studies showed that the N–C bond formation is followed by the C–C bond formation. The indium-catalyzed annulation reaction thus starts with the nucleophilic attack of the NH2 group of o-acylanilines to the MeO-connected carbon atom of the heteroaryl ring in an SNAr fashion, and thereby the N–C bond is formed. The resulting intermediate then cyclizes to make the C–C bond through the nucleophilic attack of the heteroaryl-ring-based carbon atom to the carbonyl carbon atom, providing the HA[b]Q after aromatizing dehydration. Full article
(This article belongs to the Special Issue Indium in Organic Synthesis)
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11 pages, 672 KiB  
Communication
Catalytic Annulation of Epoxides with Heterocumulenes by the Indium-Tin System
by Itaru Suzuki, Akira Imakuni, Akio Baba and Ikuya Shibata
Molecules 2018, 23(4), 782; https://doi.org/10.3390/molecules23040782 - 28 Mar 2018
Cited by 6 | Viewed by 4254
Abstract
In the synthesis of five-membered heterocycles by the annulation of epoxides with heterocumulenes such as carbon dioxide and isocyanates, we developed the indium-tin catalytic system and synthesized various cyclic adducts including novel types products under mild reaction conditions. Full article
(This article belongs to the Special Issue Indium in Organic Synthesis)
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Review

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18 pages, 16287 KiB  
Review
Selective Double Addition Reaction of an E‒H Bond (E = Si, B) to a C≡N Triple Bond of Organonitriles
by Masumi Itazaki and Hiroshi Nakazawa
Molecules 2018, 23(11), 2769; https://doi.org/10.3390/molecules23112769 - 25 Oct 2018
Cited by 14 | Viewed by 3732
Abstract
The catalytic double hydrometalation such as hydrosilylation and hydroborylation of organonitriles has attracted considerable attention because the obtained products are widely used in organic synthesis and it is thought to be one of the effective methods for reduction of organonitriles. However, the examples [...] Read more.
The catalytic double hydrometalation such as hydrosilylation and hydroborylation of organonitriles has attracted considerable attention because the obtained products are widely used in organic synthesis and it is thought to be one of the effective methods for reduction of organonitriles. However, the examples of these reactions are quite limited to date. This paper summarizes the development of selective double hydrosilylation, double hydroborylation, and dihydroborylsilylation of organonitriles, including their reaction mechanisms and the role of the metal species in the catalytic cycle. Full article
(This article belongs to the Special Issue Indium in Organic Synthesis)
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