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Department of Chemistry

Tuesday Lunchtime Research Meetings 2017-18

The meeting will usually start at 12 noon with a buffet lunch, with talks starting at 12:30. More details will be provided by email just before the event.

31 October 2017

“Lytic Reactions Of Lipid Membranes”

by John Sanderson (https://www.dur.ac.uk/chemistry/staff/profile/?id=198)

“On the move: molecular rearrangement and macroscopic motion”

by Matt Kitching (https://www.dur.ac.uk/chemistry/staff/profile/?id=15807)

(Matt and John’s talks are aimed to coincide with the biophysical theme of the annual Howard Prize Lecture that takes place in the New Ogden Physics building later in the day: https://www.dur.ac.uk/bsi/events/?eventno=36558)

7 November 2017

“Integrative Modelling of Macromolecular Assemblies”

by Matteo Degiacomi (https://degiacomi.org)

“Transient absorption: a general tool for probing excited states”

by Allie Tyson (JRRV group www.verlet.net)

14 November 2017

Light Activated Nanomachines for Targeted Therapeutics

by Robert Pal (https://www.dur.ac.uk/chemistry/staff/profile/?id=6011)

Fluorescent retinoids for cell biology and beyond

by David Chisholm (AW group https://www.dur.ac.uk/chemistry/staff/profile/?id=204)

28 November 2017

The synthesis, characterisation and properties of triplet harvesting emissive organic molecules

by Jonathan Ward (MRB group https://www.dur.ac.uk/chemistry/staff/profile/?id=172)

Finding needles in haystacks: sea cucumbers, reaction monitoring; and more

by Juan Aguilar (https://www.dur.ac.uk/chemistry/staff/profile/?id=11141)

THURSDAY 14 December 2017

lunch from 1 pm with talk starting at 1:15 pm

Manipulating controlled radical polymerization to control architecture, functionality and morphology

by Athina Anastasaki (University of California, Santa Barbara https://scholar.google.co.uk/citations?user=wFpF2_kAAAAJ&hl=en)

Abstract

In this talk the development of new controlled radical polymerization strategies will be presented, including atom transfer radical polymerization (ATRP), reversible addition-fragmentation chain transfer (RAFT) polymerization and emulsion polymerization. These synthetic strategies give access to advanced materials consisting of hydrophilic, hydrophobic, semi-fluorinated and functional segments. Although traditional polymerization strategies require various parameters to be optimized to achieve a high degree of control over molecular weight and dispersity, this work demonstrates that one set of universal conditions can be achieved. These universal conditions result in efficacious polymerization of different classes of monomers, including acrylates, methacrylates and styrene. The facile nature of these conditions, combined with readily available reagents, will greatly expand the availability of tailored polymeric materials to all researchers. Ultimately, the synthesis of complex, sequence-controlled multiblock copolymers will reveal advanced materials that exhibit unique characteristics and morphologies.

23 January 2018

running 10 am - 5 pm

"Drug Discovery and Delivery II"

A day-long meeting supported by Durham University; Universidade Federal do Rio de Janeiro, Brasil; The Royal Society and the Global Challenges Research Fund
A meeting schedule is available to download below.

Resources

30 January 2018

"Polarisation and order in biological networks: equilibrium and (some) dynamics"

by Kristian Müller-Nedebock, Dept of Physics, Stellenbosch University South Africa (www)

The mechanical and transport properties of a cell depend on the precise nature of networks which make up the cytoskeleton. The distribution and orientation of filaments within the finite region of the cell also vary with position within the cell and can be imaged. Molecular dynamics simulations show that confinement affects the orientation and distribution of filaments within the cell [Azari, A. & Müller-Nedebock, K. K. EPL (2015)]. A monomer ensemble technique allows us to understand branching and cross-linking in finite networks consisting of stiff filaments. We also briefly discuss active cross-linkers in networks, restricting our view to the one-dimensional contractile ring, and two-dimensional motility assays [Mebwe Pachong, S. & Müller-Nedebock, K. K. EPJE (2017)].

AND

"Fluid transport through fluid tubes"

by Buddhapriya Chakrapati, Department of Physics, University of Sheffield (www)

Motivated by experiments I will talk about some recent ideas to understand fluid flow through nano-fluidic channels.

20 February 2018

"Challenging Catalytic C–H Bond Activation"

by Uwe Schneider, University of Edinburgh (www)

13 March 2018

"Sex, drugs and rock ‘n’ roll: the secret life of Euglena gracilis"

by Ellis O'Niel University of Oxford (www)

FRIDAY 4 May 2018

Synthetic chemistry mini-symposium

Musgrave Room, 11:30 – 15:10

11:30-12:10 Dr Adam Calow, Bower Group, University of Bristol, "Medium ring lactams via N-directed carbonylative C-C bond activation"

New methods for the activation and functionalization of relatively inert covalent bonds (e.g. C-H and C-C) have been of growing interest in recent years. These methodologies offer chemists new strategies for the construction of sp3-rich organic scaffolds. The Bower group has developed strategies for the carbonylative activation of cyclopropanes, which gives access to rhodacyclopentanones (an sp3-rich class of metallacycle). These rhodacyclopentanones can be trapped by pendant π-nucleophiles, giving access to nitrogen-rich organic scaffolds (e.g. pyrrolidines,azocanes, azepines and 1,3-diazepanes). This presentation will introduce the first nitrogen-directed carbonylative C-C bond activations of benzo-fused and non-fused aminocyclopropanes. This gives direct access to challenging 7- and 8-membered lactams.

12:10-12:50 Jay Wright, PGS Group, Durham University, "Regioselective Borylation of Heterocycles"

Organoboron compounds are of great importance to organic, medicinal and materials chemistry, representing key intermediates for the introduction of a wide variety of functional groups. This is best exemplified by the Suzuki-Miyaura cross-coupling. In recent years, the direct C-H borylation of arenes has become an attractive method for the synthesis of aryl boronate esters. However, this transformation is more challenging for heterocycles bearing an azinyl nitrogen atom, where the presence of the nitrogen lone pair can inhibit the reaction. This is particularly evident at the proximal C-H bond, where C-H activation often does not occur. Whilst many heterocycles have been investigated, aminopyrazoles remain underexplored. This nucleus features in an array of bioactive molecules, such as herbicides, anti-cancer, and anti-parastic drugs. In this presentation, we will describe a simple method for the selective C-H functionalization at both azinyl and remote C-H positions of 3- and 5- aminopyrazoles.

Lunch break sponsored by Buchi

13:30-14:10 Dr Na (Anna) Wu, Guangxi Normal University in Guilin, China (currently visiting Oxford)

"Transition-metal catalysed enynes domino (cascade) reactions"

Polycyclic skeletons (alkaloids, lactones, indenones) have broad use as bioactive agents. However, supplylimitations from natural sources often mean chemical synthesis is key to derivingnew medicines from these leads. This requires synthetic efficiency, such as'domino' strategies which enable the formation of multiple bonds in a single step. The transition-metal catalysis projects (mainly palladium) here explores new domino reactions which areconnected by the principle of reaction initiation through nucleopalladationto access polycyclic structures in a stereo-,chemo- and regioselective manner. We hope to extend these principles to sequenced multicomponent reactions, which form multiple bonds and rings in one transformationin the future.

14:10-15:10 ProfessorJean-François Soulé, University of Rennes, France, "Transition Metal-Catalyzed C–H Bond Functionalization: Application to the Synthesis of Life and Material Molecules"

Transition-metal-mediated direct coupling via C-H bond cleavage is currently one of the most active areas in organic synthesis.1 We found that appropriately (hetero)aromatic substrates such as (poly)fluorobenzene, thiophenes, selenophenes, pyrroles, and benzoxazoles can undergo palladium catalyzed direct coupling with benzenesulfonyl chlorides and/or aryl bromides via regioselective C-H bond cleavage allowing the straightforward preparation of pharmaceutical motifs1 and organic materials precursors.2 We have developed methods that can target multiple different C–H bonds on heterocycles using catalyst and/ or reagent control to define simultaneously how each site is regioselectively modified based on electronic factor rather than employ a directing group.3 Such procedures have been extent to iterative process for the synthesis of polycyclic organic molecules.4 We also apply C–H bond functionalization in the late stage modifications ligands for the preparation of new catalytic systems.5
1. a) F. Abdellaoui, C. Youssef, H. Ben Ammar, T. Roisnel, J.-F. Soulé, H. Doucet, ACS Catal. 2016, 6, 4248; b) T. Yan, L. Zhao, M. He, J.-F. Soulé, C. Bruneau, H. Doucet, Adv. Synth. Catal. 2014, 356, 1586; c)
2. a) I. Idris, F. Derridj, J.-F. Soulé, H. Doucet, Adv. Synth. Catal. 2017, 359, 2448 ; b) A. Skhiri, R. B. Salem, J.-F. Soulé, H. Doucet, Chem. Eur. J. 2017, 23, 2788; c) I. Idris, T. Tannoux, F. Derridj, V. Dorcet, J. Boixel, V. Guerchais, J.-F. Soulé, H. Doucet, J. Mater. Chem. C 2018, Advance Article.
3. a) K. Yuan, J.-F. Soulé, H. Doucet, ACS Catal. 2015, 5, 978 ; b) R. Jin, K. Yuan, E. Chatelain, J.-F. Soulé, H. Doucet, Adv. Synth. Catal. 2014, 356, 3831, c) A. Hfaiedh, K. Yuan, H. Ben Ammar, B. Ben Hassine, J.-F. Soulé, H. Doucet, ChemSusChem 2015,8, 1794; d) A. Skhiri, A. Beladhria, K. Yuan, J.-F. Soulé, R. Ben Salem, H. Doucet, Eur. J. Org. Chem. 2015, 4428.
4. a) K. Yuan, J.-F. Soulé, V. Dorcet, H. Doucet, ACS Catal. 2016, 8121b) W. Hagui, N. Besbes, E. Srasra, T. Roisnel, J.-F. Soulé, H. Doucet, Org. Lett. 2016, 18, 4182; c) W. Hagui, K. Yuan, N. Besbes, E. Srasra, J.-F. Soulé, H. Doucet, chemCatChem2015, 7, 3544 d) X. Shi, T. Roisnel, J.-F. Soule, H. Doucet, Org. Chem. Front. 2018, 5, 398.

5. a) M. Brahim, H. Ben Ammar, V. Dorcet, J.-F. Soulé, H. Doucet, Org. Lett. 2017, 19, 2584; b) C.-S. Wang, T. Roisnel, P. H. Dixneuf, J.-F. Soulé, Org. Lett. 2017, 19, 6720; c) C.-S. Wang, P. H. Dixneuf, J.-F. Soulé, ChemCatChem 2017,9, 3117

15:10 tea and discussions

8 May 2018

"From metal-free cross-couplings to radical cyclization cascades: new methods for synthesis"

Prof. David Procter, University of Manchester (www)

MONDAY 14 May 2018

"Process Understanding: A Tool in Chemical Process Development"

Dr Ian Ashworth, AstraZeneca, Macclesfield

"Photochemistry on a Computer"

Dr Basile Churchod, Durham (www)

22 May 2018

"Molecular tug-of-war: promoting reactions with force"

Dr Guiliaume De Bo, University of Manchester (www)

Mechanical force is a formidable, and relatively unexplored, source of energy that, with its ability to distort, bend and stretch chemical bonds, is unique in the way it activates chemical reactions. The precise control of this force could revolutionise how we build and rearrange molecules and change the way we think about chemical transformations. Pulling both ends of a macromolecule apart creates highly directional strain with its highest intensity in the middle of the chain and, in polymer mechanochemistry, the force is transduced to force-sensitive moieties (mechanophores) embedded within the polymeric backbone. The activation can be performed on a single molecule using force microscopies or in bulk with the help of flow fields or ultrasound activation. The latter technique has led to remarkable achievements in the last decade, such as being able to: bias reaction pathways, trap reactive intermediates, activate catalysts, or induce chemiluminescence. Our research aims at creating new mechanophores for application in synthetic chemistry, materials and biology.
Relevant publications
(1) De Bo, G. Chem. Sci. 2018, 82, 4433.
(2) Stevenson, R.; De Bo, G. J. Am. Chem. Soc. 2017, 139, 16768–16771.

"Gel-Based Approaches to Novel Crystal Forms"

Prof. Jonathan Steed, Durham (www)

FRIDAY 6th July

Mini-Symposium on boron-catalysed amidation: from theory to practice

10.00-10.30 Professor Henry Rzepa, Imperial College, London

"Computational catalysis: mechanistic reality checks"

Computational chemistry can provide valuable reality checks for unravelling the mechanistic basis for catalytic processes. The process will be illustrated for reaction pathways of boron-based amidation catalysts and reagents, the use of calculated 11B NMR chemical shifts for helping to identify putative reaction intermediates and the publication of FAIR data archives as part of the scholarly publication processes.

10.30-11.15 Dr Tom Sheppard, University College, London

"Borate esters as highly effective catalysts for direct amidation"

Simple borate esters such as B(OMe)3and B(OCH2CF3)3were found to very effective catalysts for mediating the direct amidation between carboxylic acids and amines. The reactions have an extremely wide substrate scope, and can be carried out very efficiently on large scale to produce multigram quantities of amide. The presentation will cover the development of this reaction, along with insights into the reaction mechanisms.

11.15-11.45 Coffee

11.45-12.45 Professor Ishihara Kazuaki, Nagoya University, Japan

"Rational design of high performance catalysts using boron Lewis acids"

We have studied on rational design of high performance catalysts based on acid–base combination chemistry. In this lecture, two topics will be focused. One is “Boronic Acid Catalysts for Dehydrative Condensation between Carboxylic Acids and Amines.”1The other is “Boron Lewis Acid-assisted Chiral Brønsted Acid Catalysts for Enantioselective Cycloadditions.”2
1. (a) Wang, K.; Yanhui, Lu, Ishihara, K. to be submitted. (b) Yanhui, L.; Wang, K.; Ishihara, K. Asian J. Org. Chem. 2017, 6, 1111. (c) Ishihara, K.; Yanhui, L. Chem. Sci. 2017, 7, 1276.
2. (a)Hatano, M.; Sakamoto, T.; Ishihara, K. to be submitted. (b) Sakamoto, T.; Mochizuki, T.; Goto, Y.; Hatano, M.; Ishihara, K.Chem. Asian J. 2018,13,in press. (c) Hatano, M.; Hayashi, K.; Sakamoto, T.; Makino, Y.; Ishihara, K. Synlett 2016, 27, 1061. (d) Hatano, M.; Ishihara, H.; Goto, Y.; Ishihara, K. Synlett 2016, 27, 564. (e) Hatano, M.; Goto, Y.; Izumiseki, A.; Akakura, M.; Ishihara, K. J. Am. Chem. Soc. 2015, 137, 13472. (f) Hatano, M.; Mizuno, T.; Izumiseki, A.; Usami, R.; Asai, T.; Akakura, M.; Ishihara, K. Angew. Chem. Int. Ed. 2011, 50, 12189.

12.45 Buffet lunch and discussion