Professor King Kuok (Mimi) Hii

Rix K, Kelsall GH, Hellgardt K, Hii Ket al., 2015, Chemo- And diastereoselectivities in the electrochemical reduction of maleimides, ChemSusChem, Vol: 8, Pages: 665-671, ISSN: 1864-5631

The electrochemical cathodic reduction of cyclic imides (maleimides) to succinimides can be achieved chemoselectively in the presence of alkene, alkyne, and benzyl groups. The efficiency of the system was demonstrated by using a 3D electrode in a continuous flow reactor. The reduction of 3,4-dimethylmaleimides to the corresponding succinimides proceeds with a 3:2 diastereomeric ratio, which is independent of the nitrogen substituent and electrode surface area. The stereoselectivity of the process was rationalized by using DFT calculations, involving an acid-catalyzed tautomerization of a half-enol occurring through a double hydrogen-transfer mechanism.

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Brechtelsbauer Clemens, Hii King Kuok Mimi, 2014, 1. Catalysis in flow, ISBN: 9783110367508

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Barreiro EM, Boltukhina EV, White AJP, Hii Ket al., 2014, Atropisomeric [(diphosphine)Au2Cl2] complexes and their catalytic activity towards asymmetric cycloisomerisation of 1,6-enynes, Chemistry - A European Journal, Vol: 21, Pages: 2686-2690, ISSN: 0947-6539

KGaA. X-ray crystal structures of two [(diphosphine)-Au2Cl2] complexes (in which diphosphine = P-Phos and xylyl-P-Phos; P-Phos = [2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine]) were determined and compared to the reported structures of similar atropisomeric gold complexes. Correlations between the Au⋯Au distances and torsional angles for the biaryl series of ligands (MeOBIPHEP, SEGPhos, and P-Phos; BIPHEP = 2,2′-bis(diphenylphosphino)-1,1′-biphenyl, SEGPhos = [(4,4′-bi-1,3-benzodioxole)-5,5′-diyl]-bis[diphenylphosphine]) can be made; these measurements appear to be very dependent upon the phosphorous substituent. Conversely, the same effect was not observed for ligands based on the binaphthyl (BINAP) series. The catalytic activity of these complexes was subsequently assessed in the enantioselective cycloisomerisation of 1,6-enynes and revealed an over-riding electronic effect: more-electron-rich phosphines promote greater enantioselectivity. The possibility of silver acting as a (co-)catalyst was ruled out in these reactions.

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Brazier JB, Nguyen BN, Adrio LA, Barreiro EM, Leong WP, Newton MA, Figueroa SJA, Hellgardt K, Hii KKMet al., 2014, Catalysis in flow: <i>Operando</i> study of Pd catalyst speciation and leaching, CATALYSIS TODAY, Vol: 229, Pages: 95-103, ISSN: 0920-5861

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• Citations: 46

Kurbangalieva A, Carmichael D, Hii KKM, Jutand A, Brown JMet al., 2014, Oxidative Addition to Palladium(0) Diphosphine Complexes: Observations of Mechanistic Complexity with Iodobenzene as Reactant, CHEMISTRY-A EUROPEAN JOURNAL, Vol: 20, Pages: 1116-1125, ISSN: 0947-6539

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• Citations: 28

Taylor LL, Goldberg FW, Hii KK, 2013, Erratum: Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction (Organic and Biomolecular Chemistry (2012) 10 (4424-4432) DOI: 10.1039/c2ob25122a), Organic and Biomolecular Chemistry, Vol: 11, ISSN: 1477-0520

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Taylor LL, Goldberg FW, Hii KKM, 2013, Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction (vol 10, pg 4424, 2012), ORGANIC & BIOMOLECULAR CHEMISTRY, Vol: 11, Pages: 8506-8506, ISSN: 1477-0520

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Sheshenev AE, Boltukhina EV, Grishina AA, Cisarova I, Lyapkalo IM, Hii KKMet al., 2013, New Chiral Zwitterionic Phosphorus Heterocycles: Synthesis, Structure, Properties and Application as Chiral Solvating Agents, CHEMISTRY-A EUROPEAN JOURNAL, Vol: 19, Pages: 8136-8143, ISSN: 0947-6539

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• Citations: 12

Dunn PJ, Hii KK, Krische MJ, Williams MTet al., 2013, Sustainable Catalysis: Challenges and Practices for the Pharmaceutical and Fine Chemical Industries, Sustainable Catalysis: Challenges and Practices for the Pharmaceutical and Fine Chemical Industries

Opens the door to the sustainable production of pharmaceuticals and fine chemicals. Driven by both public demand and government regulations, pharmaceutical and fine chemical manufacturers are increasingly seeking to replace stoichiometric reagents used in synthetic transformations with catalytic routes in order to develop greener, safer, and more cost-effective chemical processes. This book supports the discovery, development, and implementation of new catalytic methodologies on a process scale, opening the door to the sustainable production of pharmaceuticals and fine chemicals. Pairing contributions from leading academic and industrial researchers, Sustainable Catalysis focuses on key areas that are particularly important for the fine chemical and pharmaceutical industries, including chemo-, bio-, and organo-catalytic approaches to C-H, C-N, and C-C bond-forming reactions. Chapters include academic overviews of current innovations and industrial case studies at the process scale, providing new insights into green catalytic methodologies from proof-of-concept to their applications in the synthesis of target organic molecules. Sustainable Catalysis provides the foundation needed to develop sustainable green synthetic procedures, with coverage of such emerging topics as: Catalytic reduction of amides avoiding LiAlH4 or B2H6. Synthesis of chiral amines using transaminases. Industrial applications of boric acid and boronic acid catalyzed direct amidation reactions. C-H activation of heteroaromatics. Organocatalysis for asymmetric synthesis. Offering a balanced perspective on current limitations, challenges, and solutions, Sustainable Catalysis is recommended for synthetic organic chemists seeking to develop new methodologies and for industrial chemists dedicated to large-scale process development. © 2013 by John Wiley & Sons, Inc.

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Barreiro EM, Adrio LA, Hii KKM, Brazier JBet al., 2013, Coinage Metal Catalysts for the Addition of O-H to C=C Bonds, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Vol: 2013, Pages: 1027-1039, ISSN: 1434-193X

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• Citations: 42

Wong VHL, Hor TSA, Hii KKM, 2013, Silver-catalysed intramolecular hydroamination of alkynes with trichloroacetimidates, CHEMICAL COMMUNICATIONS, Vol: 49, Pages: 9272-9274, ISSN: 1359-7345

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• Citations: 40

Sheshenev AE, Boltukhina EV, Hii KKM, 2013, Levonantradol: asymmetric synthesis and structural analysis, CHEMICAL COMMUNICATIONS, Vol: 49, Pages: 3685-3687, ISSN: 1359-7345

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• Citations: 17

Sheshenev AE, Boltukhina EV, White AJP, Hii KKMet al., 2013, Methylene-Bridged Bis(imidazoline)-Derived 2-Oxopyrimidinium Salts as Catalysts for Asymmetric Michael Reactions, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, Vol: 52, Pages: 6988-6991, ISSN: 1433-7851

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• Citations: 41

Adrio LA, Nguyen BN, Guilera G, Livingston AG, Hii KKet al., 2012, Erratum: Speciation of Pd(OAc) <inf>2</inf> in ligandless Suzuki-Miyaura reaction (Catalysis Science and Technology (2012) 2 (316-323) DOI: 10.1039/c1cy00241d), Catalysis Science and Technology, Vol: 2, ISSN: 2044-4753

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• Citations: 1

Sheshenev AE, Smith AMR, Hii KKM, 2012, Preparation of dicationic palladium catalysts for asymmetric catalytic reactions, NATURE PROTOCOLS, Vol: 7, Pages: 1765-1773, ISSN: 1754-2189

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• Citations: 10

Sheshenev AE, Smith AMR, Hii KKM, 2012, Preparation of dicationic palladium catalysts for asymmetric catalytic reactions., Nat Protoc, Vol: 7, Pages: 1765-1773

The synthesis of Pd(OTf)(2)·2H(2)O is described. This was used to generate two different types of chiral dicationic palladium complexes for highly enantioselective addition of aromatic amines to α, β-unsaturated conjugate alkenes ([(R-BINAP)Pd(OH(2))(2)][OTf](2) and [(R-BINAP)Pd(μ-OH)](2)[OTf](2)). The resulting optically active N-arylated β-amino acid derivatives are valuable synthetic intermediates for the synthesis of biologically active molecules and peptidomimetics. The reaction of (2E)-but-2-enoylcarbamate and aniline is shown as an example of the use of these catalysts for enantioselective aza-Michael addition. For the preparation of palladium(II) triflate, the time scale is 20 h 50 min, plus 5 h 15 min for the monomeric complex and plus 6 h 45 min for the dimeric complex.

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Arbour JL, Rzepa HS, Contreras-Garcia J, Adrio LA, Barreiro EM, Hii KKMet al., 2012, Silver-Catalysed Enantioselective Addition of O-H and N-H Bonds to Allenes: A New Model for Stereoselectivity Based on Noncovalent Interactions, CHEMISTRY-A EUROPEAN JOURNAL, Vol: 18, Pages: 11317-11324, ISSN: 0947-6539

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• Citations: 40

Barreiro EM, Broggini DFD, Adrio LA, White AJP, Schwenk R, Togni A, Hii KKMet al., 2012, Gold(I) Complexes of Conformationally Constricted Chiral Ferrocenyl Phosphines, ORGANOMETALLICS, Vol: 31, Pages: 3745-3754, ISSN: 0276-7333

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• Citations: 28

Nguyen BN, Adrio LA, Barreiro EM, Brazier JB, Haycock P, Hii KK, Nachtegaal M, Newton MA, Szlachetko Jet al., 2012, Deconvolution of the Mechanism of Homogeneous Gold-Catalyzed Reactions, Organometallics, Vol: ASAP

The role of chiral counterions in gold-catalyzed asymmetric intramolecular hydroamination/hydroalkoxylation reactions of allenes and the oxidation state of the gold catalyst in the benzannulation of 2-carbonylphenylalkynes have been investigated using XAFS at the L3 edge of gold. Fitting of experimental data indicated a bond between cationic gold and a BINOL-phosphate anion in solution. 31P NMR confirmed that this phosphate group is likely not to be labile and may stay bonded to the gold catalyst during the catalytic cycle. In the benzannulation reaction, XAFS analysis suggested the majority of gold species obtained from reacting starting material with AuCl3 to be Au(III) complexes. NMR and mass spectrometry characterization led to the previously unobserved intermediate 10. gem-Diaurate complexes, which have been previously proposed as possible intermediates, were not detected.

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Adrio LA, Nguyen BN, Guilera G, Livingston AG, Hii KKMet al., 2012, Speciation of Pd(OAc)₂ in ligandless Suzuki-Miyaura reaction (vol 2, pg 316, 2012), CATALYSIS SCIENCE & TECHNOLOGY, Vol: 2, Pages: 2578-2578, ISSN: 2044-4753

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• Citations: 1

Taylor LL, Goldberg FW, Hii KKM, 2012, Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction, ORGANIC & BIOMOLECULAR CHEMISTRY, Vol: 10, Pages: 4424-4432, ISSN: 1477-0520

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• Citations: 34

Zotova N, Roberts FJ, Kelsall GH, Jessiman AS, Hellgardt K, Hii KKMet al., 2012, Catalysis in flow: Au-catalysed alkylation of amines by alcohols, GREEN CHEMISTRY, Vol: 14, Pages: 226-232, ISSN: 1463-9262

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• Citations: 55

Liu X, Hii KKM, 2011, Alternative to Benzoquinone for Room-Temperature Fujiwara-Moritani Reactions, JOURNAL OF ORGANIC CHEMISTRY, Vol: 76, Pages: 8022-8026, ISSN: 0022-3263

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• Citations: 41

Nguyen BN, Adrio LA, Guilera G, Livingston AG, Hii KKMet al., 2011, Speciation of Pd(OAc)2 in Ligandless Suzuki-Miyaura Reaction, Catalysis Science & Technology, Pages: 316-323

Generation of catalytically active Pd(0) species from Pd(OAc)2 has been examined, in the context of Suzuki–Miyaura reactions involving substitution of aryl bromides under aerobic and ambient conditions. Using a combination of spectroscopic, microscopic and kinetic measurements, the role of each reaction component is delineated in the speciation of the palladium species. Among the key findings are the effects of O2, H2O and inorganic base, and implications for catalytic activity.

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Adrio LA, Hii KKM, 2011, Palladium-Catalyzed Heterofunctionalization of C-H, C=C and C≡C Bonds, CURRENT ORGANIC CHEMISTRY, Vol: 15, Pages: 3337-3361, ISSN: 1385-2728

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• Citations: 7

Adrio LA, Hii KKM, 2011, An Expedient Synthesis of Olfactory Lactones by Intramolecular Hydroacylalkoxylation Reactions, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Vol: 2011, Pages: 1852-1857, ISSN: 1434-193X

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• Citations: 7

Smith AMR, Hii KKM, 2011, Transition Metal Catalyzed Enantioselective α-Heterofunctionalization of Carbonyl Compounds, CHEMICAL REVIEWS, Vol: 111, Pages: 1637-1656, ISSN: 0009-2665

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• Citations: 313

Zotova N, Hellgardt K, Kelsall GH, Jessiman AS, Hii KKMet al., 2010, Catalysis in flow: the practical and selective aerobic oxidation of alcohols to aldehydes and ketones, GREEN CHEMISTRY, Vol: 12, Pages: 2157-2163, ISSN: 1463-9262

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• Citations: 71

Liu X, Mimi Hii KK, 2010, Oxidative Amidation of Activated Alkenes Using Pd(OAc)₂ as a Catalyst Precursor, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Vol: 2010, Pages: 5181-5189, ISSN: 1434-193X

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• Citations: 29

Smith AMR, Rzepa HS, White AJP, Billen D, Hii KKMet al., 2010, Delineating Origins of Stereocontrol in Asymmetric Pd-Catalyzed α-Hydroxylation of 1,3-Ketoesters, JOURNAL OF ORGANIC CHEMISTRY, Vol: 75, Pages: 3085-3096, ISSN: 0022-3263

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• Citations: 89