Alan R Kennedy

University of Strathclyde, Glasgow, Scotland, United Kingdom

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Publications (474)1726.62 Total impact

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    ABSTRACT: Two thienoacene dimers based on the thieno[3,2-b]thiophene moiety were efficiently synthesized, characterized and evaluated as active hole-transporting layers in organic thin-film field-effect transistors. Both compounds behaved as active p-channel organic semi-conductors showing averaged hole mobility of up to 1.33 cm2 V−1 s−1.
    Journal of Materials Chemistry C. 12/2014;
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    ABSTRACT: Sensitive optical detection of nitroaromatic vapours with diketo-pyrrolopyrrole thin films is reported for the first time and the impact of thin film crystal structure and morphology on fluorescence quenching behaviour demonstrated.
    Chemical Communications 11/2014; · 6.38 Impact Factor
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    ABSTRACT: The regioselectivity of deprotonation reactions between arene substrates and basic metalating agents is usually governed by the electronic and/or coordinative characteristics of a directing group attached to the benzene ring. Generally, the reaction takes place in the ortho position, adjacent to the substituent. Here, we introduce a protocol by which the metalating agent, a disodium-monomagnesium alkyl-amide, forms a template that extends regioselectivity to more distant arene sites. Depending on the nature of the directing group, ortho-meta' or meta-meta' dimetalation is observed, in the latter case breaking the dogma of ortho metalation. This concept is elaborated through the characterization of both organometallic intermediates and electrophilically quenched products.
    Science 11/2014; 346(6211):834-7. · 31.48 Impact Factor
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    ABSTRACT: The effect on catalyst performance of altering substituents at the 2-position of the Macmillan imidazolidinone has been examined. Condensation of L-phenylalanine N-methyl amide with acetophenone derivatives results in a series of imidazolidinones whose salts can be used to accelerate the Diels-Alder cycloaddition. Electron withdrawing groups significantly increases the overall rate of cycloaddition without compromise in selectivity. The most effective catalyst was shown to be efficient for a variety of substrates and the applicability of this catalyst to alternative secondary amine catalysed transformations is also discussed.
    Organic & Biomolecular Chemistry 10/2014; · 3.49 Impact Factor
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    ABSTRACT: Proton transfer to the sulfa drug sulfadiazine [systematic name: 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide] gave eight salt forms. These are the monohydrate and methanol hemisolvate forms of the chloride (2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium chloride monohydrate, C10H11N4O2S+·Cl−·H2O, (I), and 2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium chloride methanol hemisolvate, C10H11N4O2S+·Cl−·0.5CH3OH, (II)); a bromide monohydrate (2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium bromide monohydrate, C10H11N4O2S+·Br−·H2O, (III)), which has a disordered water channel; a species containing the unusual tetraiodide dianion [bis(2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium) tetraiodide, 2C10H11N4O2S+·I42−, (IV)], where the [I4]2− ion is located at a crystallographic inversion centre; a tetrafluoroborate monohydrate (2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium tetrafluoroborate monohydrate, C10H11N4O2S+·BF4−·H2O, (V)); a nitrate (2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium nitrate, C10H11N4O2S+·NO3−, (VI)); an ethanesulfonate {4-[(pyrimidin-2-yl)sulfamoyl]anilinium ethanesulfonate, C10H11N4O2S+·C2H5SO3−, (VII)}; and a dihydrate of the 4-hydroxybenzenesulfonate {4-[(pyrimidin-2-yl)sulfamoyl]anilinium 4-hydroxybenzenesulfonate dihydrate, C10H11N4O2S+·HOC6H4SO3−·2H2O, (VIII)}. All these structures feature alternate layers of cations and of anions where any solvent is associated with the anion layers. The two sulfonate salts are protonated at the aniline N atom and the amide N atom of sulfadiazine, a tautomeric form of the sulfadiazine cation that has not been crystallographically described before. All the other salt forms are instead protonated at the aniline group and on one N atom of the pyrimidine ring. Whilst all eight species are based upon hydrogen-bonded centrosymetric dimers with graph set R22(8), the two sulfonate structures also differ in that these dimers do not link into one-dimensional chains of cations through NH3-to-SO2 hydrogen-bonding interactions, whilst the other six species do. The chloride methanol hemisolvate and the tetraiodide are isostructural and a packing analysis of the cation positions shows that the chloride monohydrate structure is also closely related to these.
    Acta Crystallographica Section C. 09/2014;
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    ABSTRACT: Vinyl cyclopropane rearrangement (VCPR) has been utilised to synthesise a difluorinated cyclopentene stereospecifically and under mild thermal conditions. Difluorocyclopropanation chemistry afforded ethyl 3-(1'(2'2'-difluoro-3'-phenyl)cyclopropyl) propenoate as all four stereoisomers (18a, 18b, 22a, 22b) (all racemic). The trans-E isomer (18a), prepared in 70 % yield over three steps, underwent near quantitative VCPR to difluorocyclopentene 23 (99 %). Rearrangements were monitored by (19) F NMR (100-180 °C). While cis/trans cyclopropane stereoisomerisation was facile, favouring trans-isomers by a modest margin, no E/Z alkene isomerisation was observed even at higher temperatures. Neither cis nor trans Z-alkenoates underwent VCPR, even up to much higher temperatures (180 °C). The cis-cyclopropanes underwent [3,3]-rearrangement to afford benzocycloheptadiene species. The reaction stereospecificity was explored by using electronic structure calculations, and UB3LYP/6-31G* methodology allowed the energy barriers for cyclopropane stereoisomerisation, diastereoisomeric VCPR and [3,3]-rearrangement to be ranked in agreement with experiment.
    Chemistry 09/2014; · 5.70 Impact Factor
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    ABSTRACT: 1-lithio-2-butyl-1,2-dihydropyridines, typically formed as intermediates in the nucleophilic substitution (addition/elimination) of pyridine with (n- or t-) butyl lithium, have been isolated and comprehensively characterized. The linear substituted isomer is polymeric while the branched substituted isomer is a cyclotrimer. The lower oligomerization of the latter complex confers exceptional hexane solubility making it an excellent lithium hydride source in non-polar, aliphatic media.
    Chemical Communications 09/2014; · 6.38 Impact Factor
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    ABSTRACT: The chemistry of the hydrotris(mercaptobenzothiazolyl)borate anion (Tbz) with metal salts (HgI2, SbI3, BiI3, CoCl2) is reported in an attempt to probe the stability of the of Tbz ligand once coordinated to hard and soft metals. Complexes of Tbz with bismuth, containing the [Bi(Tbz)I3](-) anion, are stable, but with the other metals this is not the case. Although simple complexes such as [Hg(Tbz)I] and [E(Tbz)I3](-) (E = Sb, Bi) can be isolated from the reaction mixtures, subsequent reactions lead to ligand modification or decomposition. In the presence of mercury and antimony we observe the formation of a hitherto unseen cationic pentacyclic heterocycle. With cobalt we observe a small quantity of a product which suggests a more complete decomposition. A simple benzothiazole (bz) adduct [Co(bz)2Cl2] has been identified, in which the Tbz ligand has disintegrated and the parent heterocycle, mercaptobenzothiazole, has been desulfurized. A rationale for these observations is given.
    Inorganic Chemistry 09/2014; · 4.79 Impact Factor
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    ABSTRACT: Using structurally defined potassium- tetra(alkyl)magnesiates, a new straightforward methodology to promote regioselective Mg-H exchange reactions of a wide range of aromatic and heteroaromatic substrates is disclosed. Contacted ion pair intermediates are likely to be involved, with K being the key to facilitate the magnesiation processes.
    Chemical Communications 09/2014; · 6.38 Impact Factor
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    ABSTRACT: A general thermolysis reaction for the transformation of Group 1 TMP compounds (LiTMP, NaTMP, KTMP) to 1-aza-allylic TTHP derivatives is reported. TMEDA accelerates the reaction and produces the crystalline complexes [(TMEDA)LiTTHP] and [(TMEDA·NaTTHP)2]. Methane elimination during the transformational process was confirmed via TVA coupled to MS.
    Chemical Communications 07/2014; · 6.72 Impact Factor
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    ABSTRACT: Control over solid state structure is critical for effective performance in optoelectronic devices bearing π-conjugated charge mediating organic materials. A series of five structurally related N-benzyl-substituted diketopyrrolopyrroles (DPPs) differing solely in 2 out their 60 atoms were synthesized and crystal structures obtained. Systematic variation of the long axis aligned, π−π stacks has been identified within the single crystal structure series and intermolecular interaction energies and charge transfer integrals for the π−π stacks have been computed by means of density functional theory (M06-2X/6-311G(d)). The computed intermolecular interaction energies as well as charge transfer integrals were further investigated utilizing a series of systematically cropped dimer pairs, highlighting the crucial role of the benzyl/halo substitution on stabilization of these π−π dimers. Two of the DPPs, including a new polymorph of a previously reported structure exhibit twice the intermolecular interaction energy and comparable hole transfer integrals to Rubrene, one of the most efficient hole conducting materials known. The computed properties for all of the π−π dimer systems reported herein are consistent with trends predicted by a model system. As such these materials show great promise as charge mediators in organic electronic applications and may be exploited in systematic structure activity based investigations of charge transfer theory. ■ INTRODUCTION Diketopyrrolopyrrole derivatives are widely employed in the pigment industry 1−3 and have seen an increasing surge of interest as charge transfer mediators in field effect transis-tors, 4−9 as well as dye-based solar cell technologies. 10−16 We are currently engaged in the development of small molecule diketopyrrolopyrrole platforms in novel optoelectronic and sensing applications. In π-conjugated charge mediating organic systems, crystal engineering by means of control of molecular solid state organization and crystal structure are critical for effective device performance. 17−19 Small changes in molecular structure can have a dramatic impact on those intermolecular electronic interactions which influence key charge transport properties such as charge transfer integrals in organic conducting materials. 20,21 Despite their wide study, there remains an identified need to examine in more detail the impact of systematic structural variation on DPP crystal structures and how that thereby influences the emergence of semiconductor bands in these organic materials. 18 The detailed mechanism accounting for charge transport in organic conducting materials is the subject of considerable debate. 22,23
    Crystal Growth & Design 07/2014; · 4.56 Impact Factor
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    ABSTRACT: A general thermolysis reaction for the transformation of Group 1 TMP compounds (LiTMP, NaTMP, KTMP) to 1-aza-allylic TTHP derivatives is reported. TMEDA accelerates the reaction and produces the crystalline complexes [(TMEDA)LiTTHP] and [(TMEDANaTTHP)2]. Methane elimination during the transformational process was confirmed via TVA coupled to MS.
    Chemical Communications 07/2014; · 6.38 Impact Factor
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    ABSTRACT: A systematic study both in the solid- and solution-state, was carried out for a series of sodium magnesiates containing the utility amide ligand 1,1,1,3,3,3-hexamethyldisilazide (HMDS). The first complex considered is the donor-free bisamido monoalkyl polymeric complex [Na(μ-HMDS)2Mg((n)Bu)]∞. The reactivity of with common tertiary bidentate donors including N,N,N',N'-tetramethylethylenediamine (TMEDA) or its chiral relative (1R,2R)-tetramethylcyclohexyldiamine [(R,R)-TMCDA] is detailed. Surprisingly, the products of these reactions are not simple diamine adducts but are solvent separated sodium magnesiate systems [(TMEDA)2·Na](+)[Mg(HMDS)3](-) and [{(R,R)-TMCDA}2·Na](+)[Mg(HMDS)3](-). By concentrating on the likely equilibria which may give rise to formation of , a potential intermediate complexed ion pair [{(TMEDA)2·Na}(μ-(n)Bu)Mg(HMDS)2] was isolated. Additionally, the novel "inverse magnesiates" [{Na(μ-HMDS)}2Mg(μ-(n)Bu)2·(TMEDA)]∞ and [{Na(μ-HMDS)}2Mg(μ-(n)Bu)2·{(R,R)-TMCDA}]∞, were obtained by reacting solutions of composition "NaMg(HMDS)((n)Bu)2" (a likely by-product in the formation of from ), with TMEDA or (R,R)-TMCDA. The structure and nature of these bimetallic complexes have been determined using a combination of X-ray crystallographic studies and multinuclear NMR spectroscopy.
    Dalton Transactions 07/2014; · 4.10 Impact Factor
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    ABSTRACT: Expanding the synthetic potential of Mg–Zn hybrid organyl reagents (generated via transmetallation reactions), this study uncovers a versatile approach, involving a sequence of direct Zn–I exchange and Pd catalysed cross-coupling reactions which grants access to a wide range of asymmetric bis(aryls). By combining X-ray crystallography with ESI-MS and non-deuterium NMR spectroscopic studies, new light is shed on the heterobimetallic constitution of the intriguing organometallic species [(THF)4MgCl2Zn(tBu)Cl] (1) and [{Mg2Cl3(THF)6}+{ZntBu3}−] (2), formed through transmetallation of tBuMgCl with n equivalent amounts of ZnCl2 (n = 1 and 3 respectively). Operating by cooperative effects, alkyl-rich hybrid 2 can effectively promote direct Zn–I exchange reactions with aromatic halides in short periods of time at room temperature in THF solution. The structural elucidation of key organometallic intermediates involved in some of these Zn–I exchanges, provides new reactivity insights into how these bimetallic systems operate. Thus, while the reaction of 2 with 3 equivalents of 2-iodoanisole (3b) gives magnesium dizincate [{Mg(THF)6}2+{Zn(o-C6H4-OMe)3}2−] (4) which demonstrates the 3-fold activation of the tBu groups attached to Zn in 2, using 2-iodobenzonitrile (3i), only two tBu groups react with the substrate, affording [(THF)4MgCl(NC-o-C6H4)ZnI(o-C6H4-CN)(THF)] (7). In 7 Mg and Zn are connected by an aryl bridge, suggesting that the formation of contacted ion-pair hybrids may have a deactivating effect on the outcome of the Zn–I exchange process. A wide range of homoleptic tris(aryl) zincate intermediates have been prepared in situ and used as precursors in Pd catalysed cross-coupling reactions, affording bis(aryls) 6a–s in excellent yields under mild reaction conditions without the need of any additive or polar cosolvent such as NMP or DMI.
    Chemical Science 06/2014; · 8.60 Impact Factor
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    ABSTRACT: Previously it was reported that activation of (t)Bu2Zn by [(TMEDA)Na(μ-dpa)]2 led to tert-butylation of benzophenone at the challenging para-position, where the sodium amide functions as a metalloligand towards (t)Bu2Zn manifested in crystalline [{(TMEDA)Na(dpa)}2Zn(t)Bu2] (TMEDA is N,N,N',N'-tetramethylethylenediamine, dpa is 2,2'-dipyridylamide). Here we find altering the Lewis donor or alkali metal within the metalloligand dictates the reaction outcome, exhibiting a strong influence on alkylation yields and reaction selectivity. Varying the former led to the synthesis of three novel complexes, [(PMDETA)Na(dpa)]2, [(TMDAE)Na(dpa)]2, and [(H6-TREN)Na(dpa)], characterised through combined structural, spectroscopic and theoretical studies [where PMDETA is N,N,N',N'',N''-pentamethyldiethylenetriamine, TMDAE is N,N,N',N'-tetramethyldiaminoethylether and H6-TREN is N',N'-bis(2-aminoethyl)ethane-1,2-diamine]. Each new sodium amide can function as a metalloligand to generate a co-complex with (t)Bu2Zn. Reacting these new co-complexes with benzophenone proved solvent dependent with yields in THF much lower than those in hexane. Most interestingly, sub-stoichiometric amounts of the metalloligands [(TMEDA)Na(dpa)]2 and [(PMEDTA)Na(dpa)]2 with 1 : 1, (t)Bu2Zn-benzophenone mixtures produced good yields of the challenging 1,6-tert-butyl addition product in hexane (52% and 53% respectively). Although exchanging Na for Li gave similar reaction yields, the regioselectivity was significantly compromised; whereas the K system was completely unreactive. Replacing (t)Bu2Zn with (Me3SiCH2)2Zn shut down the alkylation of benzophenone; in contrast, (t)BuLi generates only the reduction product, benzhydrol. Zincation of the parent amine dpa(H) generated the crystalline product [Zn(dpa)2], as structurally elucidated through X-ray crystallography and theoretical calculations. Although the reaction mechanism for the alkylation of benzophenone remains unclear, incorporation of the radical scavenger TEMPO (2,2,6,6-tetramethylpiperidine-N-oxyl radical) into the reaction system completely inhibits benzophenone alkylation.
    Dalton Transactions 06/2014; · 4.10 Impact Factor
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    ABSTRACT: Using an interlocking co-complexation approach, a homologous series of unsolvated alkali-metal zincates [MZn(CH2SiMe3)3] (M = Li , Na , K ) was prepared by reacting equimolar amounts of Zn(CH2SiMe3)2 with the relevant alkali-metal alkyl M(CH2SiMe3) employing non-coordinating hexane as a solvent. X-ray crystallographic studies reveal that these heterobimetallic compounds exhibit unprecedented supramolecular assemblies made up exclusively of a three-fold combination of M-CH2, Zn-CH2 and MMe interactions. Revealing an important alkali-metal effect, displays a linear chain structure; whereas and form much more intricate 3D and 2D coordination networks respectively. Shedding new light into the formation of these solvent-free zincates, DFT calculations indicate that the infinite degree of aggregation observed in plays a major role in thermodynamically driving the co-complexation reactions of their homometallic precursors. NMR spectroscopic studies suggest that in C6D6 solution exist as discrete contacted ion-pair species, where the alkali-metal is partially solvated by molecules of deuterated solvent. The supramolecular assemblies of can be easily deaggregated by adding the polydentate N-donors PMDETA (N,N,N',N'',N''-pentamethyldiethylenetriamine) or TMEDA (N,N,N',N'-tetramethylethylenediamine), affording monomeric [(PMDETA)LiZn(CH2SiMe3)3] () and [(TMEDA)2NaZn(CH2SiMe3)3] ().
    Dalton Transactions 06/2014; · 4.10 Impact Factor
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    ABSTRACT: Reported here are the single-crystal X-ray structure analyses of bis-μ-methanol-κ(4)O:O-bis{[hydrotris(3-phenyl-2-sulfanylidene-2,3-dihydro-1H-1,3-imidazol-1-yl)borato-κ(3)H,S,S'](methanol-κO)sodium(I)}, [Na2(C27H22BN6S3)2(CH4O)4] (NaTm(Ph)), bis-μ-methanol-κ(4)O:O-bis{[hydrotris(3-isopropyl-2-sulfanylidene-2,3-dihydro-1H-1,3-imidazol-1-yl)borato-κ(3)H,S,S'](methanol-κO)sodium(I)}-diethyl ether-methanol (1/0.3333/0.0833), [Na2(C18H28BN6S3)2(CH4O)4]·0.3333C4H10O·0.0833CH3OH (NaTm(iPr)), and a novel anhydrous form of sodium hydrotris(methylthioimidazolyl)borate, poly[[μ-hydrotris(3-methyl-2-sulfanylidene-2,3-dihydro-1H-1,3-imidazol-1-yl)borato]sodium(I)], [Na(C12H16BN6S3)] ([NaTm(Me)]n). NaTm(iPr) and NaTm(Ph) have similar dimeric molecular structures with κ(3)H,S,S'-bonding, but they differ in that NaTm(Ph) is crystallographically centrosymmetric (Z' = 0.5) while NaTm(iPr) contains one crystallographically centrosymmetric dimer and one dimer positioned on a general position (Z' = 1.5). [NaTm(Me)]n is a one-dimensional coordination polymer that extends along the a direction and which contains a hitherto unseen side-on η(2)-C=S-to-Na bond type. An overview of the structural preferences of alkali metal soft scorpionate complexes is presented. This analysis suggests that these thione-based ligands will continue to be a rich source of interesting alkali metal motifs worthy of isolation and characterization.
    Acta crystallographica. Section C, Structural chemistry. 05/2014; 70(Pt 5):421-7.
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    ABSTRACT: The title compound, C11H8N2O3S, shows two mol-ecules per asymmetric unit, with the dihedral angles between the benzene and thio-phene rings of 13.53 (6) and 8.50 (5)° being a notable difference between them. An intra-molecular N-H⋯O hydrogen-bond in each mol-ecule generates an S(6) ring motif. The crystal packing shows no classical hydrogen bonds with the mol-ecules being packed to form weak C-H⋯O and C-H⋯S inter-actions leading to R 2 (2)(9) and R 4 (4)(25) rings which are edge-shared, giving layers parallel to (010).
    Acta Crystallographica Section E Structure Reports Online 05/2014; 70(Pt 5):o613. · 0.35 Impact Factor
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    ABSTRACT: Synthetically important for introducing a picolyl scaffold into a molecular construction, alkali metallated picoline (methylpyridine) complexes are also interesting in their own right for the diversity of their ligand-metal bonding possibilities. Here the syntheses of seven new such complexes are reported: namely three 4-picoline derivatives 4-picLi·Me6TREN, , 4-picNa·Me6TREN, , and [4-picK·2(4-picH)]∞, ; and four 2-picoline derivatives, 2-picLi·Me6TREN, , 2-picLi·PMDETA, , 2-picNa·Me6TREN, , and [2-picK·PMDETA]2, [where pic = NC5H4(CH2); Me6TREN = tris(N,N-dimethyl-2-aminoethyl)amine, (Me2NCH2CH2)3N; PMDETA = N,N,N',N'',N''-pentamethyldiethylenetriamine, (Me2NCH2CH2)2NMe]. X-ray crystallographic studies establish that the lighter alkali metal complexes , , and adopt monomeric structures in contrast to the polymeric and dimeric arrangements adopted by potassium complexes and respectively. All complexes have also been characterized by solution NMR spectroscopy ((1)H, (13)C, and where relevant (7)Li). This study represents the first example of sodium and potassium picolyl complexes to be isolated and characterized. DOSY (Diffusion-Ordered Spectroscopy) experiments performed on and suggest both compounds retain their monomeric constitutions in C6D6 solution. Discussion focuses on the influence of the metal and neutral donor molecule on the structures and the nature of the ligand-metal (enamido versus aza-allylic) interactions.
    Dalton Transactions 04/2014; · 4.10 Impact Factor
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    ABSTRACT: Despite their enormous synthetic relevance, the use of polar organolithium and Grignard reagents is greatly limited by their requirements of low temperatures in order to control their reactivity as well as the need of dry organic solvents and inert atmosphere protocols to avoid their fast decomposition. Breaking new ground on the applications of these commodity organometallics in synthesis under more environmentally friendly conditions, this work introduces deep eutetic solvents (DESs) as a green alternative media to carry out chemoselective additions of ketones in air at room temperature. Comparing their reactivities in DES with those observed in pure water suggest that a kinetic activation of the alkylating reagents is taking place, favoring nucleophilic addition over the competitive hydrolysis, which can be rationalized through formation of halide-rich magnesiate or lithiate species.
    Angewandte Chemie 04/2014;

Publication Stats

2k Citations
1,726.62 Total Impact Points


  • 1996–2014
    • University of Strathclyde
      • Department of Pure and Applied Chemistry
      Glasgow, Scotland, United Kingdom
  • 2012–2013
    • Erciyes Üniversitesi
      • Department of Physics
      Kayseri, Kayseri, Turkey
    • Universidad Santiago de Cali
      Santiago de Cali, Valle del Cauca, Colombia
  • 2001–2012
    • Newcastle University
      • School of Chemistry
      Newcastle upon Tyne, ENG, United Kingdom
  • 2011
    • University of Bath
      • Department of Chemistry
      Bath, ENG, United Kingdom
  • 2010
    • Kano University of Science & Technology
      Wudil, Kano, Nigeria
  • 2003–2010
    • Universidad de La Laguna
      • Department of Organic Chemistry
      San Cristóbal de La Laguna, Canary Islands, Spain
  • 2009
    • Spanish National Research Council
      • Instituto de Productos Naturales y Agrobiología
      Madrid, Madrid, Spain
  • 2007–2009
    • Johannes Gutenberg-Universität Mainz
      • Institute of Inorganic and Analytical Chemistry
      Mainz, Rhineland-Palatinate, Germany
  • 2005–2007
    • University of Notre Dame
      • Department of Chemistry and Biochemistry
      United States