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1. Integrating biochemical and behavioral approaches to develop a bait to manage the invasive yellow paper wasp Polistes versicolor (Hymenoptera, Vespidae) in the Galápagos Islands

Author

Mariana Bulgarella, Alejandro E. Mieles, Jacqueline Rodríguez, Yesenia Campaña, Georgia M. Richardson, Robert A. Keyzers, Charlotte E. Causton, and Philip J. Lester

Subjects
Attractants, body part extracts, invasive species, semiochemicals, social wasps, Ecology, QH540-549.5, General. Including nature conservation, geographical distribution, QH1-199.5
Abstract

It is estimated that more than 500 species of insects have been introduced to the Galápagos Islands via human activities. One of these insect invaders is the yellow paper wasp, Polistes versicolor (Olivier) (Hymenoptera: Vespidae), a social wasp native to continental South America. In Galápagos, these wasps are voracious predators of insect larvae, compete with native species for insect prey or for floral resources and are a human nuisance. Wasp suppression methods currently in use are inefficient and attract non-target species, calling for the development of species-specific attractants that can be used in baits to lure and kill wasps. To evaluate the potential for using wasp semiochemicals in baits, we determined the biochemical composition of the head, thorax, Dufour’s and venom glands of P. versicolor foragers via gas chromatography/mass spectrometry (GC/MS). Male and female wasps were tested for behavioral responses to body segment extracts from both sexes. Female body extracts consistently elicited more behavioral responses in both male and female wasps than male extracts. Females reacted to female head, thorax and abdomen (the Dufour’s and venom glands are located in the abdomen) extracts, whereas males reacted significantly to female head and thorax extracts. One male body extract, the head, elicited two significant behaviors: female wasps groomed more often, and males touched the filter paper more often compared to the blank control. Head extracts consistently changed the behavior of female and male wasps and, together with female thorax extracts, have potential as species-specific lures for yellow paper wasps. Heads were mainly composed of hydrocarbon lipids and oleamide, a ligand for odorant-binding proteins. The thorax consisted of fatty aldehydes, long-chain alkanes and fatty amide lipids. Field trials of blends of these compounds in high wasp density areas of Galápagos are the next step to confirm if any of these compounds are attractive to P. versicolor.

Published
2022
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2. Hydroarylation of olefins catalysed by a dimeric ytterbium(II) alkyl

Author

Georgia M. Richardson, Iskander Douair, Scott A. Cameron, Joe Bracegirdle, Robert A. Keyzers, Michael S. Hill, Laurent Maron, and Mathew D. Anker

Subjects
Science
Abstract

Nucleophilic alkylation of aromatics with main group reagents was achieved, but it is limited to a stoichiometric regime. Here, the authors report that the ytterbium(II) hydride reacts with ethene and propene to afford ytterbium(II) n-alkyls, both of which can facilitate the catalytic alkylation of benzene at room temperature via an SN2 mechanism.

Published
2021
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3. Ytterbium (II) Hydride as a Powerful Multielectron Reductant

Author

Iskander Douair, Scott A. Cameron, Laurent Maron, Mathew D. Anker, Georgia M. Richardson, Victoria University of Wellington, Laboratoire de physique et chimie des nano-objets (LPCNO), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Fédération de recherche « Matière et interactions » (FeRMI), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Ytterbium, polyaromatic hydrocarbons, Hydrogen, Hydride, multielectron reduction, Organic Chemistry, naphthalene, Aromatization, chemistry.chemical_element, General Chemistry, Photochemistry, Catalysis, chemistry.chemical_compound, 7-cyclooctatetraene, Deprotonation, chemistry, ytterbium hydrides, Density functional theory, [PHYS.PHYS.PHYS-CHEM-PH]Physics [physics]/Physics [physics]/Chemical Physics [physics.chem-ph], Naphthalene
Abstract

International audience; A dimeric beta-diketiminato ytterbium(II) hydride affects both the two-electron aromatization of 1,3,5,7-cyclooctatetraene (COT) and the more challenging two-electron reduction of polyaromatic hydrocarbons, including naphthalene (E-0=-2.60 V). Confirmed by Density Functional Theory calculations, these reactions proceed via consecutive polarized Yb-H/C=C insertion and deprotonation steps to provide the respective ytterbium (II) inverse sandwich complexes and hydrogen gas. These observations highlight the ability of a simple ytterbium(II) hydride to act as a powerful two-electron reductant at room temperature without the necessity of an external electron to initiate the reaction and avoiding radicaloid intermediates.

Published
2021

4. Reactivity of a β-diketiminate ytterbium(II) hydride with cyclopentadiene derivatives

Author

Georgia M. Richardson, Jesse Howarth, Matthew J. Evans, Alison J. Edwards, Scott A. Cameron, and Mathew David Anker

Subjects
Materials Chemistry, Physical and Theoretical Chemistry
Abstract

Cyclopentadienyl ligands are ubiquitous in lanthanide chemistry and have been used extensively to stabilize low-valent lanthanide(II) complexes. We now report the reactions of the β-diketiminate ytterbium(II) hydride [(BDIDipp)Yb(H)]2 (BDIDipp = HC{C(Me)NDipp}2, Dipp = 2,6-iPr2C6H3) with tetramethylcyclopentadiene, pentamethylcyclopentadiene, indene, and fluorene; to provide ready access to the heteroleptic ytterbium(II) η5-C5R5 cyclopentadienides with extrusion of hydrogen gas. The tetramethylcyclopentadienyl, pentamethylcyclopentadienyl, indenyl, and fluorenyl compounds were characterized by 1H and 13C{1H} NMR, elemental analysis, and single crystal X-ray diffraction. These data indicated that each heteroleptic cyclopentadienide exists as a mononuclear species in both solution and the solid state, formulated with retention of the oxidation state on the ytterbium(II) center. Additionally, the pentamethylcyclopentadienyl derivative was characterized by single crystal neutron diffraction, a study that explored the nature of an agostic interaction between a methyl group and the ytterbium(II) center.

Published
2022
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5. Hydroarylation of olefins catalysed by a dimeric ytterbium(II) alkyl

Author

Laurent Maron, Iskander Douair, Mathew D. Anker, Georgia M. Richardson, Robert A. Keyzers, Joe Bracegirdle, Michael S. Hill, Scott A. Cameron, Victoria University of Wellington, Laboratoire de physique et chimie des nano-objets (LPCNO), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Fédération de recherche « Matière et interactions » (FeRMI), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), University of Bath [Bath], AINSE Early Career Research Grant, AINSE Honours Scholarship, Curtis-Gordon Research Scholarship, Dr. Margaret L. Bailey Award, and Victoria University of Wellington Doctoral Scholarship

Subjects
Catalyst synthesis, Science, General Physics and Astronomy, Alkylation, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, General Biochemistry, Genetics and Molecular Biology, Article, Catalysis, Propene, chemistry.chemical_compound, Nucleophile, Reactivity (chemistry), Benzene, Multidisciplinary, 010405 organic chemistry, Hydride, [CHIM.ORGA]Chemical Sciences/Organic chemistry, General Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, Homogeneous catalysis, 0104 chemical sciences, chemistry, SN2 reaction, lipids (amino acids, peptides, and proteins)
Abstract

Although the nucleophilic alkylation of aromatics has recently been achieved with a variety of potent main group reagents, all of this reactivity is limited to a stoichiometric regime. We now report that the ytterbium(II) hydride, [BDIDippYbH]2 (BDIDipp = CH[C(CH3)NDipp]2, Dipp = 2,6-diisopropylphenyl), reacts with ethene and propene to provide the ytterbium(II) n-alkyls, [BDIDippYbR]2 (R = Et or Pr), both of which alkylate benzene at room temperature. Density functional theory (DFT) calculations indicate that this latter process operates through the nucleophilic (SN2) displacement of hydride, while the resultant regeneration of [BDIDippYbH]2 facilitates further reaction with ethene or propene and enables the direct catalytic (anti-Markovnikov) hydroarylation of both alkenes with a benzene C-H bond., Nucleophilic alkylation of aromatics with main group reagents was achieved, but it is limited to a stoichiometric regime. Here, the authors report that the ytterbium(II) hydride reacts with ethene and propene to afford ytterbium(II) n-alkyls, both of which can facilitate the catalytic alkylation of benzene at room temperature via an SN2 mechanism.

Published
2021

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