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Development and Application of Aryne Chemistry 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 August 2015) | Viewed by 39403

Special Issue Editors


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Guest Editor
Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan
Interests: copper catalysis; borylation; stannylation; silylation; main group organometallics; cross-coupling; multicomponent coupling; aryne chemistry
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Guest Editor
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607, USA
Interests: natural product synthesis; new reaction development; metathesis chemistry; aryne chemistry; reactivity of alkylidene carbenes

Special Issue Information

Dear Colleagues,

Since 1902, arynes, as highly reactive transient molecules, have been recognized as useful reactive intermediates in synthetic organic chemistry. In particular, the last decade has witnessed a remarkable progress in aryne chemistry through new mechanistic understanding and synthetic applications; this has occurred by and large via the use of Kobayashi’s silylaryl triflates as aryne precursors. In addition, arynes have proven to be good substrates for transition metal-catalyzed reactions and multicomponent coupling reactions, enabling the construction of various molecular frameworks consisting natural products, pharmaceuticals, and other organic materials of importance. This Special Issue welcomes submissions of research articles covering all areas of aryne chemistry dealing with synthetic application, development new reactions, mechanistic insights, computational studies, and other related subjects.

Prof. Dr. Hiroto Yoshida
Prof. Dr. Daesung Lee
Guest Editors

Manuscript Submission Information

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Keywords

  • catalytic reactions of aryne
  • coupling reactions of aryne with nucleophile
  • multicomponent reactions of aryne
  • pericyclic reactions of aryne
  • aryne in total synthesis

Published Papers (4 papers)

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Research

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795 KiB  
Communication
Selective Halogen-Lithium Exchange of 1,2-Dihaloarenes for Successive [2+4] Cycloadditions of Arynes and Isobenzofurans
by Shohei Eda and Toshiyuki Hamura
Molecules 2015, 20(10), 19449-19462; https://doi.org/10.3390/molecules201019449 - 23 Oct 2015
Cited by 16 | Viewed by 8883
Abstract
Successive [2+4] cycloadditions of arynes and isobenzofurans by site-selective halogen-lithium exchange of 1,2-dihaloarenes were developed, allowing the rapid construction of polycyclic compounds which serve as a useful synthetic intermediates for the preparation of various polyacene derivatives. Full article
(This article belongs to the Special Issue Development and Application of Aryne Chemistry in Organic Synthesis)
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889 KiB  
Communication
Synthesis of Phenolic Compounds by Trapping Arynes with a Hydroxy Surrogate
by Rajdip Karmakar, Sourav Ghorai, Yuanzhi Xia and Daesung Lee
Molecules 2015, 20(9), 15862-15880; https://doi.org/10.3390/molecules200915862 - 31 Aug 2015
Cited by 26 | Viewed by 8373
Abstract
Trapping of arynes with various nucleophiles provides a range of heteroatom-functionalized arene derivatives, but the corresponding reaction with water does not provide phenol derivatives. Silver trifluroacetate (AgO2CCF3) can nicely solve this problem. It was found that in typical organic [...] Read more.
Trapping of arynes with various nucleophiles provides a range of heteroatom-functionalized arene derivatives, but the corresponding reaction with water does not provide phenol derivatives. Silver trifluroacetate (AgO2CCF3) can nicely solve this problem. It was found that in typical organic solvent, AgO2CCF3 readily reacts with arynes to generate trifluoroacetoxy organosilver arene intermediate, which, upon treating with silica gel, provides phenolic products. This protocol can be extended to the synthesis of α-halofunctionalized phenol derivatives by simply adding NBS (N-bromosuccinimides) or NIS (N-iodosuccinimides) to the reaction along with silver trifluroacetate, which provided α-bromo or α-iodophenol derivatives in good yield. However, the similar reactions with NCS (N-chlorosuccinimides) afforded only the protonated product instead of the expected α-chlorophenols derivatives. Interestingly, substrates containing silyl substituents on 1,3-diynes resulted in α-halotrifluoroacetates rather than their hydrolyzed product. Additionally, trapping the same arynes with other oxygen-based nucleophiles containing silver counter cation, along with NXS (N-halosuccinimides), generated α-halooxyfunctionalized products. Full article
(This article belongs to the Special Issue Development and Application of Aryne Chemistry in Organic Synthesis)
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1213 KiB  
Communication
An Alternative Method for Generating Arynes from ortho-Silylaryl Triflates: Activation by Cesium Carbonate in the Presence of a Crown Ether
by Suguru Yoshida, Yuki Hazama, Yuto Sumida, Takahisa Yano and Takamitsu Hosoya
Molecules 2015, 20(6), 10131-10140; https://doi.org/10.3390/molecules200610131 - 1 Jun 2015
Cited by 59 | Viewed by 10984
Abstract
An alternative method for generating arynes from ortho-silylaryl triflates using cesium carbonate and 18-crown-6 is reported. The method was efficiently applied to a variety of reactions between several arynes and arynophiles. We also demonstrated that the efficiency of aryne generation is significantly [...] Read more.
An alternative method for generating arynes from ortho-silylaryl triflates using cesium carbonate and 18-crown-6 is reported. The method was efficiently applied to a variety of reactions between several arynes and arynophiles. We also demonstrated that the efficiency of aryne generation is significantly affected by the alkali metal countercation of the carbonate. Full article
(This article belongs to the Special Issue Development and Application of Aryne Chemistry in Organic Synthesis)
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Review

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1072 KiB  
Review
Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes
by Hideto Miyabe
Molecules 2015, 20(7), 12558-12575; https://doi.org/10.3390/molecules200712558 - 9 Jul 2015
Cited by 52 | Viewed by 9706
Abstract
Most of the synthetic approaches to the benzo-fused heterocycles containing an oxygen atom have involved the use of phenol derivatives as a starting material. This review highlights the new synthetic approaches involving the aromatic C-O bond-forming process using arynes. The insertion of arynes [...] Read more.
Most of the synthetic approaches to the benzo-fused heterocycles containing an oxygen atom have involved the use of phenol derivatives as a starting material. This review highlights the new synthetic approaches involving the aromatic C-O bond-forming process using arynes. The insertion of arynes into the C=O bond gives the unstable intermediates, [2 + 2] cycloaddition-type adducts, which can be easily converted into a variety of oxygen atom-containing heterocycles in a single operation. In this review, the syntheses of oxygen heterocycles, such as coumarin, chromene, xanthene, dihydrobenzofuran and benzofuran derivatives, via the insertion of arynes into the C=O bond of aldehydes or formamides are summarized. Full article
(This article belongs to the Special Issue Development and Application of Aryne Chemistry in Organic Synthesis)
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