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Special Issue "Alkynes: From Reaction Design to Applications 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 October 2018

Special Issue Editor

Guest Editor
Prof. Dr. Igor V. Alabugin

Department of Chemistry and Biochemistry, Florida State University, Tallahassee, USA
Website | E-Mail
Interests: organic reaction mechanisms; stereoelectronic effects; organic photochemistry; DNA photocleavage; carbon-rich materials; chemistry of alkynes; radical chemistry; cyclizations; cycloaromatizations; cycloadditions

Special Issue Information

Dear Colleagues,

Alkyne functionality represents one of the most valuable building blocks of organic chemistry. Despite its seeming simplicity, it combines many unusual and attractive features. For example, the compact carbon-rich alkyne moiety stores >60 kcal/mol of potential energy. Furthermore, alkynes have the same oxidation state as carbonyl compounds and, hence, via simple addition of nucleophiles, offer a “hidden door” entry into carbonyl chemistry. Due to the presence of two independently addressable π-systems, alkynes can readily form four (and, under certain conditions, up to six) new bonds, lending themselves perfectly to the design of cascade transformations. The recent examples of unusual alkyne transformations include ionic chemistry of neutral hydrocarbons, preparation of radicals without radical initiators, generation of excited states without light, "1,2-dicarbene reactivity" of alkynes in "boomerang" radical processes, selective conversion of alkynes into carbonyl compounds, and full disassembly of the alkyne moiety. With the advent of modern catalytic methods, it seems that new reactions of alkynes are discovered every day.

Recognizing the hidden connections between the fundamental features of alkynes and their rich reactivity is essential for uncovering the full potential of this functionality in organic synthesis. The goal of this Special Issue to is to bring multiple examples of new alkyne reactions under one cover to catalyze cross-pollination of ideas for the future development of alkyne chemistry. This issue will contain contributions that cover all aspects of alkyne structure, reactivity, and applications in organic synthesis.

Prof. Dr. Igor V. Alabugin
Guest Editor

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

  • alkynes
  • cascade transformations
  • catalysis
  • addition

Published Papers (3 papers)

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Research

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Open AccessCommunication Highly Efficient Recyclable Sol Gel Polymer Catalyzed One Pot Difunctionalization of Alkynes
Molecules 2018, 23(8), 1879; https://doi.org/10.3390/molecules23081879
Received: 19 June 2018 / Revised: 23 July 2018 / Accepted: 24 July 2018 / Published: 27 July 2018
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Abstract
Amino-bridged gel polymer P1 was discovered to catalyze alkyne halo-functionalization in excellent yields, regioselectivity, functional group compatibility, and recyclability. We have observed that both aromatic and aliphatic alkynes can be converted to α,α-dihalogenated ketones in the presence of polymer P1 under metal-free conditions
[...] Read more.
Amino-bridged gel polymer P1 was discovered to catalyze alkyne halo-functionalization in excellent yields, regioselectivity, functional group compatibility, and recyclability. We have observed that both aromatic and aliphatic alkynes can be converted to α,α-dihalogenated ketones in the presence of polymer P1 under metal-free conditions at room temperature within a short reaction time. Full article
(This article belongs to the Special Issue Alkynes: From Reaction Design to Applications in Organic Synthesis)
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Open AccessArticle Vinylation of a Secondary Amine Core with Calcium Carbide for Efficient Post-Modification and Access to Polymeric Materials
Molecules 2018, 23(3), 648; https://doi.org/10.3390/molecules23030648
Received: 16 February 2018 / Revised: 9 March 2018 / Accepted: 9 March 2018 / Published: 13 March 2018
Cited by 1 | PDF Full-text (1804 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
We developed a simple and efficient strategy to access N-vinyl secondary amines of various naturally occurring materials using readily available solid acetylene reagents (calcium carbide, KF, and KOH). Pyrrole, pyrazole, indoles, carbazoles, and diarylamines were successfully vinylated in good yields. Cross-linked and
[...] Read more.
We developed a simple and efficient strategy to access N-vinyl secondary amines of various naturally occurring materials using readily available solid acetylene reagents (calcium carbide, KF, and KOH). Pyrrole, pyrazole, indoles, carbazoles, and diarylamines were successfully vinylated in good yields. Cross-linked and linear polymers were synthesized from N-vinyl carbazoles through free radical and cationic polymerization. Post-modification of olanzapine (an antipsychotic drug substance) was successfully performed. Full article
(This article belongs to the Special Issue Alkynes: From Reaction Design to Applications in Organic Synthesis)
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Review

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Open AccessReview Acetylene in Organic Synthesis: Recent Progress and New Uses
Molecules 2018, 23(10), 2442; https://doi.org/10.3390/molecules23102442
Received: 16 August 2018 / Revised: 14 September 2018 / Accepted: 17 September 2018 / Published: 24 September 2018
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Abstract
Recent progress in the leading synthetic applications of acetylene is discussed from the prospect of rapid development and novel opportunities. A diversity of reactions involving the acetylene molecule to carry out vinylation processes, cross-coupling reactions, synthesis of substituted alkynes, preparation of heterocycles and
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Recent progress in the leading synthetic applications of acetylene is discussed from the prospect of rapid development and novel opportunities. A diversity of reactions involving the acetylene molecule to carry out vinylation processes, cross-coupling reactions, synthesis of substituted alkynes, preparation of heterocycles and the construction of a number of functionalized molecules with different levels of molecular complexity were recently studied. Of particular importance is the utilization of acetylene in the synthesis of pharmaceutical substances and drugs. The increasing interest in acetylene and its involvement in organic transformations highlights a fascinating renaissance of this simplest alkyne molecule. Full article
(This article belongs to the Special Issue Alkynes: From Reaction Design to Applications in Organic Synthesis)
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