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Organics, Volume 3, Issue 3

2022 September - 13 articles

Cover Story: The excellent hydrogen transfer performance of proton-responsive azairidacycles prepared from cumylamine derivatives enables the hydrodefluorination of polyfluorobenzenes and polyfluoropyridines with HCOOK at ambient temperature. Under the optimized conditions, monodefluorination of pentafluoropyridine proceeded rapidly with up to a turnover number of 418 within 1 h. In addition, high regio- and chemoselectivities were demonstrated in the comparative studies using the cyano- and chloro-substituted substrates. The C–F bond cleavage took place favorably at the para position of substituents other than fluorine, which is in consonance with the nucleophilic aromatic substitution mechanism. View this paper
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Articles (13)

  • Review
  • Open Access
20 Citations
10,884 Views
44 Pages

Recent Developments in Stereoselective Reactions of Sulfonium Ylides

  • Mukulesh Mondal,
  • Sophie Connolly,
  • Shi Chen,
  • Shubhanjan Mitra and
  • Nessan J. Kerrigan

15 September 2022

This review describes advances in the literature since the mid-1990s in the area of reactions of sulfonium ylide chemistry, with particular attention paid to stereoselective examples. Although the chemistry of sulfonium ylides was first popularized a...

  • Review
  • Open Access
2 Citations
3,418 Views
16 Pages

9 September 2022

Chloropupukeananin is a natural product that inhibits HIV-1 replication and has antitumor activity. Its structure consists of a chlorinated tricyclo[4.3.1.03,7]decane core skeleton with an array of highly oxidized multifunctional groups. In the biosy...

  • Article
  • Open Access
2 Citations
3,024 Views
11 Pages

6 September 2022

Oligomeric ellagitannins are challenging synthetic targets due to the need for an abundant supply of their composed monomeric ellagitannins and a synthetic methodology to connect them. This work focused on the divergent synthesis of the four monomeri...

  • Article
  • Open Access
3 Citations
2,191 Views
12 Pages

2 September 2022

The [3+2] cycloaddition reaction of N-aryl-C-carbamoylnitrone (nitrone 1) with N-arylitaconimide (ethylene 2) was computationally studied using the B3LYP/6-31G(d) level of theory. An analysis of the different energetic profiles and the transition sta...

  • Communication
  • Open Access
3 Citations
3,599 Views
6 Pages

31 August 2022

Diaryliodonium salts are useful arylating reagents that have been exploited widely. In this Communication, we demonstrate that heating diphenyliodonium triflate in the solvent DMSO leads to an unexpected arylation reaction. It is postulated that aryl...

  • Article
  • Open Access
5 Citations
3,098 Views
13 Pages

Dihydrooxazine Byproduct of a McMurry–Melton Reaction en Route to a Synthetic Bacteriochlorin

  • Vy-Phuong Tran,
  • Nobuyuki Matsumoto,
  • Phattananawee Nalaoh,
  • Haoyu Jing,
  • Chih-Yuan Chen and
  • Jonathan S. Lindsey

8 August 2022

A synthetic route to gem-dimethyl-substituted bacteriochlorins—models of native bacteriochlorophylls—relies on the formation of a dihydrodipyrrin precursor via a series of established reactions: van Leusen pyrrole formation, Vilsmeier for...

  • Review
  • Open Access
10 Citations
3,473 Views
22 Pages

Specific Bifunctionalization on the Surface of Phosphorus Dendrimers Syntheses and Properties

  • Massimo Petriccone,
  • Régis Laurent,
  • Cédric-Olivier Turrin,
  • Rosa Maria Sebastián and
  • Anne-Marie Caminade

3 August 2022

Dendrimers are highly branched macromolecules possessing, in most cases, identical terminal functions. However, it is sometimes desirable to have two types of surface functions in order to fulfil specific properties. The stochastic functionalization...

  • Review
  • Open Access
19 Citations
6,306 Views
30 Pages

20 July 2022

The stereoselective formation of tetrasubstituted alkenes remains one of the key goals of modern organic synthesis. In addition to other methods, the stereoselective synthesis of tetrasubstituted alkenes can be achieved by means of cross-coupling rea...

  • Article
  • Open Access
4 Citations
3,680 Views
14 Pages

Synthesis and Theoretical Studies of Aromatic Azaborines

  • Pipsa Hirva,
  • Petri Turhanen and
  • Juri M. Timonen

11 July 2022

Organoboron compounds are well known for their use as synthetic building blocks in several significant reactions, e.g., palladium-catalyzed Suzuki-Miyaura cross-coupling. As an element, boron is fascinating; as part of a molecule it structurally rese...

  • Article
  • Open Access
3 Citations
9,206 Views
9 Pages

Enantioselective Total Synthesis of Multifidene, a Sex Pheromone of Brown Algae

  • Taiki Umezawa,
  • Misaki Hara,
  • Nana Kinoshita-Terauchi and
  • Fuyuhiko Matsuda

8 July 2022

The total synthesis of multifidene, a sex pheromone found in brown algae, is described. The synthesis features the highly enantioselective and diastereoselective addition reaction of an aldehyde to a nitroolefin in the presence of a Hayashi–J&o...

  • Article
  • Open Access
4 Citations
3,912 Views
14 Pages

Mo2C as Pre-Catalyst for the C-H Allylic Oxygenation of Alkenes and Terpenoids in the Presence of H2O2

  • Michael G. Kallitsakis,
  • Dimitra K. Gioftsidou,
  • Marina A. Tzani,
  • Panagiotis A. Angaridis,
  • Michael A. Terzidis and
  • Ioannis N. Lykakis

4 July 2022

In this study, commercially available molybdenum carbide (Mo2C) was used, in the presence of H2O2, as an efficient pre-catalyst for the selective C-H allylic oxygenation of several unsaturated molecules into the corresponding allylic alcohols. Under...

  • Article
  • Open Access
2,869 Views
12 Pages

Regioselective N- versus P-Deprotonation of Aminophosphane Tungsten(0) Complexes

  • Tatjana Terschüren,
  • Philip Junker,
  • Alexander Schmer,
  • Arturo Espinosa Ferao and
  • Rainer Streubel

22 June 2022

1,2-Bifunctional ligands are rare, in general, which holds especially for those with a P-N linkage. Herein, we report on the synthesis of P-tert-butyl substituted aminophosphane W(CO)5 complexes 3a-f (a: R = R’ = H; b: R = H, R = Me; c: R = H,...

  • Article
  • Open Access
2 Citations
4,394 Views
11 Pages

22 June 2022

The catalytic hydrodefluorination (HDF) with a bifunctional azairidacycle using HCOOK was examined for cyano- and chloro-substituted fluoroarenes, including penta- and tetrafluorobenzonitriles, tetrafluoroterephthalonitrile, tetrafluorophthalonitrile...

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Organics - ISSN 2673-401X