Newcastle University

Introduction

After completing my PhD studies at University College London under the supervision of Professor Tony Deeming I moved to Waterloo, Canada to work with Professor Arthur Carty investigating small molecule activation and skeletal transformations of phosphinidine stabilized clusters and the reactivity of hydrocarbyl ligands on bimetallic phosphido-bridged complexes. Following this, I spent 2 years as a research associate with Professor Malcolm Chisholm (FRS) preparing alkyl and alkoxide supported transition metal alkylidynes, nitrides and oxides and studying their MOCVD characteristics.

Previous Positions

1994-1995 Lecturer in Inorganic Chemistry University of Wales, Swansea
1995-2001 Senior Lecturer in Inorganic Chemistry, University of Newcastle
2001-2004 Reader in Inorganic Chemistry, Queen’s University of Belfast
2004- Senior Lecturer in Inorganic Chemistry, University of Newcastle

Research Interests

Doherty Group Research Page

Current Work

We have recently synthesised and resolved Me2-CATPHOS, a novel biaryl-like diphosphine that is constructed via Diels-Alder cycloaddition. Enantiopure rhodium complexes of this diphosphine catalyse the asymmetric hydrogenation of a range of dehydroamino acid derivatives giving ee's in excess of 99%.

• Doherty S, Knight JG, Mehdi-Zodeh H. Asymmetric Carbonyl-Ene and Friedel-Crafts Reactions Catalyzed by Lewis Acid Platinum Group Metal Complexes of the Enantiopure Atropisomeric Biaryl-Like Diphosphine (R)-Me₂-CATPHOS: A Comparison with BINAP. Tetrahedron: Asymmetry 2012, 23. In Press.
• Doherty S, Knight JG, Ellison J, Weekes D, Harrington RW, Hardacre C, Manyer H. Efficient Recyclable Peroxometalate-Based Polymer Immobilised Ionic Phase Catalysts for Hydrogen Peroxide-Mediated Oxidations. Green Chemistry 2012. In Press.
• Doherty S, Knight JG, Addyman CR, Smyth CH, Ward NAB, Harrington RW. Ruthenium Complexes of k(P)- and k(P)-h⁶-Coordinated KITPHOS Monophosphines: Efficient Catalysts for the Direct Ortho Arylation of 2-Phenylpyridine and N-Phenylpyrazole with Aryl Chlorides. Organometallics 2011, 30(21), 6010-6016.
• Doherty S, Knight JG, Smyth CS, Ward NAB, Robson KJ, Tweedly S, Harrington RW, Clegg W. Efficient Cycloisomerisation of Propargyl Amides by Electrophilic Gold(I) Complexes of KITPHOS Monophosphines: A Comparative Study. Organometallics 2010, 29(18), 4139-4147.
• Doherty S, Knight JG, McGrady JP, Ferguson AM, Ward NAB, Harrington RW, Clegg W. ortho,ortho '-Substituted KITPHOS Monophosphines: Highly Efficient Ligands for Palladium-Catalyzed C-C and C-N Bond Formation. Advanced Synthesis & Catalysis 2010, 352(1), 201-211.
• Doherty S, Smyth CH, Harriman A, Harrington RW, Clegg W. Can a Butadiene-Based Architecture Compete with its Biaryl Counterpart in Asymmetric Catalysis? Enantiopure Me-CATPHOS, a Remarkably Efficient Ligand for Asymmetric Hydrogenation. Organometallics 2009, 28(3), 888-895.
• Hashmi ASK, Loos A, Littmann A, Braun I, Knight J, Doherty S, Rominger F. Gold(I) Complexes of KITPHOS Monophosphines: Efficient Cycloisomerisation Catalysts. Advanced Synthesis & Catalysis 2009, 351(4), 576-582.
• Doherty S, Knight JG, Bell AL, El-Menabawey S, Westcott S. Rhodium Complexes of (R)-Me-CATPHOS and (R)-(S)-JOSIPHOS: Highly Enantioselective Catalysts for the Asymmetric Hydrogenation of (E)- and (Z)-beta-Aryl-beta-(Enamido)phosphonates. Tetrahedron: Asymmetry 2009, 20(12), 1437-1444.
• Doherty S, Smyth CH, Harrington RW, Clegg W. Synthesis of Biaryl Diphosphines via a Stepwise Regioselective Double Diels-Alder Cycloaddition Elimination Sequence: Efficient Ligands for the Palladium-Catalyzed Amination of Aromatic Bromides. Organometallics 2009, 28(17), 5273-5276.
• Doherty S, Knight JG, Smyth CH, Harrington RW, Clegg W. Biaryl-like CATPHOS diphosphines via double diels-alder cycloaddition between 1,4-bis(diphenylphosphinoyl)buta-1,3-diyne and anthracenes: Efficient ligands for the palladium-catalyzed amination of aromatic bromides and α-arylation of ketones. Organometallics 2008, 27(8), 1679-1682.
• Doherty S, Knight JG, Smyth CH, Harrington RW, Clegg W. Electron-Rich Bicyclic Biaryl-Like KITPHOS Monophosphines via [4+2] Cycloaddition Between 1-Alkynylphosphine Oxides and Anthracene: Highly Efficient Ligands for Palladium-Catalyzed C-N and C-C Bond Formation.. Advanced Synthesis & Catalysis 2008, 350(11-12), 1801-1806.
• Doherty S, Smyth CH, Harrington RW, Clegg W. Highly enantioselective synthesis of pseudo-C-2-symmetric axially chiral biaryl diphosphines via rhodium-catalyzed double [2+2+2] cycloaddition. Organometallics 2008, 27(19), 4837-4840.
• Doherty S, Knight JG, Mcrae A, Harrington RW, Clegg W. Oxazoline-substituted prolinamide-based organocatalysts for the direct intermolecular aldol reaction between cyclohexanone and aromatic aldehydes. European Journal of Organic Chemistry 2008, (10), 1759-1766.
• Doherty S, Knight JG, Bell AL, Harrington RW, Clegg W. Asymmetric hydrogenation of ketones with ruthenium complexes of rac- and enantiopure (S,S)-1,2-bis((diphenylphosphino)methyl)cyclohexane: A comparative study with rac- and (R)-BINAP. Organometallics 2007, 26(9), 2465-2468.
• Doherty S, Knight JG, Smyth CH, Harrington RW, Clegg W. Efficient asymmetric carbonyl-ene reactions catalyzed by platinum metal lewis acid complexes of conformationally flexible NUPHOS diphosphines: A comparison with BINAP. Organometallics 2007, 26(25), 6453-6461.
• Doherty S, Knight JG, Smyth CH, Harrington RW, Clegg W. Metal-dependent reactivity of electrophilic platinum group metal lewis acid catalysts: Competitive alkene dimerization, intramolecular friedel-crafts alkylation, and carbonyl-ene reactivity. Organometallics 2007, 26(24), 5961-5966.
• Doherty S, Smyth CH, Knight JG. Modern Carbonylation Methods: Recent Developments in Alkyne Carbonylation. In: Kollar, M, ed. Modern Carbonylation Methods. Weinheim; Chichester: VCH-Wiley, 2007, pp. 251-289.
• Doherty S, Goodrich P, Hardacre C, Knight JG, Nguyen MT, Parvulescu VI, Paun C. Recyclable copper catalysts based on imidazolium-tagged bis(oxazolines): A marked enhancement in rate and enantioselectivity for Diels-Alder reactions in ionic liquid. Advanced Synthesis and Catalysis 2007, 349(6), 951-963.
• Doherty S, Knight JG, Smyth CH, Harrington RW, Clegg W. Rhodium-catalyzed double [2 + 2 + 2] cycloaddition of 1,4- bis(diphenylphosphinoyl)buta-1,3-diyne with tethered diynes: A modular, highly versatile single-pot synthesis of NU-BIPHEP biaryl diphosphines. Organic Letters 2007. , 9(23), 4925-4928.
• Doherty S, Knight JG, Smyth CH, Harrington RW, Clegg W. Asymmetric platinum group metal-catalyzed carbonyl-ene reactions: Carbon-carbon bond formation versus isomerization. Journal of Organic Chemistry 2006, 71(26), 9751-9764.
• Doherty S, Knight JG, Smyth CH, Sore NT, Rath RK, McFarlane W, Harrington RW, Clegg W. Modular synthesis of a new class of bis(amino-oxazoline) using palladium-catalyzed Buchwald-Hartwig amination methodology. Organometallics 2006, 25(18), 4341-4350.
• Doherty S, Knight JG, Betham M. The first insoluble polymer-bound palladium complexes of 2-pyridyldiphenylphosphine: Highly efficient catalysts for the alkoxycarbonylation of terminal alkynes. Chemical Communications 2006, (1), 88-90.
• Doherty S, Goodrich P, Hardacre C, Luo H-K, Nieuwenhuyzen M, Rath RK. Lewis acid platinum complexes of conformationally flexible NUPHOS diphosphines: Highly efficient catalysts for the carbonyl - Ene reaction. Organometallics 2005,24 24 5945-5955.
• Doherty S, Knight JG, Rath RK, Clegg W, Harrington RW, Newman CR, Campbell R, Amin H. Ruthenium complexes of six-electron-donor NUPHOS-Type diphosphines: Highly selective catalysts for the hydrocarboxylation of terminal alkynes. Organometallics 2005, 24(11), 2633-2644.
• Doherty S, Newman CR, Rath RK, Van Den Berg J-A, Hardacre C, Nieuwenhuyzen M, Knight JG. Comparative study of diastereoisomer interconversion in chiral BINOL-ate and diamine platinum complexes of conformationally flexible NUPHOS diphosphines. Organometallics 2004,23 5 1055-1064.
• Doherty S, Errington RJ, Housley N, Clegg W. Dimeric aluminum chloride complexes of N-alkoxyalkyl-β-ketoimines: Activation with propylene oxide to form efficient lactide polymerization catalysts. Organometallics 2004,23 10 2382-2388.
• Doherty S, Newman CR, Rath RK, Luo H-K, Nieuwenhuyzen M, Knight JG. Highly Efficient Asymmetric Lewis Acid Catalysis with Platinum Group Complexes of Conformationally Flexible 1,3-Butadiene-Bridged Diphosphines, NUPHOS. Organic Letters 2003,5 21 3863-3866.
• Doherty S, Goodrich P, Hardacre C, Luo H-K, Rooney DW, Seddon KR, Styring P. Marked enantioselectivity enhancements for Diels-Alder reactions in ionic liquids catalysed by platinum diphosphine complexes. Green Chemistry 2003, 6(1), 63-67.
• Doherty S, Robins EG, Pal I, Newman CR, Hardacre C, Rooney D, Mooney DA. Polymer-supported phosphoramidites: highly efficient and recyclable catalysts for asymmetric hydrogenation of dimethylitaconate and dehydroamino acids and esters. Tetrahedron: Asymmetry 2003, 14(11), 1517-1527.
• Doherty S, Newman CR, Hardacre C, Nieuwenhuyzen M, Knight JG. Ruthenium complexes of the 1,4-bis(diphenylphosphino)-1,3-butadiene-bridged diphosphine 1,2,3,4-Me4-NUPHOS: Solvent-dependent interconversion of four- and six-electron donor coordination and transfer hydrogenation activity. Organometallics 2003,22 7 1452-1462.
• Doherty S, Knight JG, Scanlan TH, Elsegood MRJ, Clegg W. Iminophosphines: Synthesis, formation of 2,3-dihydro-1 H-benzo[1,3]azaphosphol-3-ium salts and N-(pyridin-2-yl)-2-diphenylphosphinoylaniline, coordination chemistry and applications in platinum group catalyzed Suzuki coupling reactions and hydrosilylations. Journal of Organometallic Chemistry 2002. ,650 1-2 231-248.
• Doherty S, Robins EG, Nieuwenhuyzen M, Champkin PA, Clegg W. Palladium complexes of 2-pyridin-2-yl substituted 1,3-bis(diphenylphosphino)propane: Highly active catalysts for the room-temperature copolymerization of carbon monoxide with ethene. Organometallics 2002, 21(20), 4147-4158.
• Doherty S, Robins EG, Nieuwenhuyzen M, Knight JG, Champkin PA, Clegg W. Synthesis of a new class of 1,4-bis(diphenylphosphino)-1,3-butadiene bridged diphosphine, NUPHOS, via zirconium-mediated reductive coupling of alkynes and diynes: Applications in palladium-catalyzed cross-coupling reactions. Organometallics 2002,21 7 1383-1399.
• Simon Doherty,* Edward G. Robins, Julian G. Knight, Colin R. Newman, Barrie Rhodes, Paul A. Champkin, William Clegg. Selectivity for the methoxy-carbonylation of ethylene versus CO-ethylene copolymerization with catalysts based on C4-bridged bidentate phosphines and phospholes. Journal of Organometallic Chemistry 2001, 640, 182-196.
• Doherty S, Knight JG, Robins EG, Scanlan TH, Champkin PA, Clegg W. Zirconium-mediated synthesis of a new class of 1,4-bis(diphenylphosphino)-1,3-butadiene-bridged diphosphine, NUPHOS: Highly efficient catalysts for palladium-mediated cross couplings. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 2001, 123(21), 5110-5111.
• Doherty S. Conversion of σ,η-allenyl group into a σ,σ-(Diphenylphosphino)allyl and a hexa-1,3,5-triene-2,6-diyl ligand at a diiron center. Organometallics 2000, 19(26), 5696-5708.
• Doherty S. Organometallic chemistry of bi- and poly-nuclear complexes. Annual Reports on the Progress of Chemistry - Section A 2000, 96, 409-440.
• Doherty S. Reactions of alkynes with [Fe2(CO)6(μ-PPh2){μ-η 1:η2α,β=(H)C α=Cβ=CγH2}]: Formation of diphenylvinylphosphine-functionalized vinyl carbenes via carbon-carbon and carbon-phosphorus bond formation and hydrogen migration. Organometallics 2000, 19(22), 4557-4562.
• Knight JG, Doherty S, Harriman A. Remarkable differences in catalyst activity and selectivity for the production of methyl propanoate versus CO-ethylene copolymer by a series of palladium complexes of related C4-bridged diphosphines. Organometallics 2000, 19(24), 4957-4967.