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Special Issue "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: 30 May 2018

Special Issue Editors

Guest Editor
Prof. Dr. Akio Baba

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

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
Website | E-Mail
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 papers will be 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 monthly 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 1800 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 (3 papers)

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Research

Open AccessFeature PaperCommunication In(III)-TMSBr-Catalyzed Cascade Reaction of Diarylalkynes with Acrylates for the Synthesis of Aryldihydronaphthalene Derivatives
Molecules 2018, 23(4), 979; https://doi.org/10.3390/molecules23040979
Received: 20 March 2018 / Revised: 19 April 2018 / Accepted: 20 April 2018 / Published: 23 April 2018
PDF Full-text (1316 KB) | HTML Full-text | XML Full-text | Supplementary Files
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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Figure 1

Open AccessArticle Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives
Molecules 2018, 23(4), 838; https://doi.org/10.3390/molecules23040838
Received: 9 March 2018 / Revised: 25 March 2018 / Accepted: 31 March 2018 / Published: 5 April 2018
PDF Full-text (1736 KB) | HTML Full-text | XML Full-text | Supplementary Files
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)
Figures

Graphical abstract

Open AccessCommunication Catalytic Annulation of Epoxides with Heterocumulenes by the Indium-Tin System
Molecules 2018, 23(4), 782; https://doi.org/10.3390/molecules23040782
Received: 15 March 2018 / Revised: 27 March 2018 / Accepted: 28 March 2018 / Published: 28 March 2018
PDF Full-text (672 KB) | HTML Full-text | XML Full-text
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)
Figures

Graphical abstract

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