Publications

Research articles and reviews

63. Catalytic Enantioselective Synthesis of Heterocyclic Vicinal Fluoroamines Using Asymmetric Protonation: A Method Development and Mechanistic Study

M. W. Ashford, C. Xu, J. J. Molloy, C. Carpenter-Warren, A. M. Z Slawin, A. G. Leach, and A. J. B. Watson, ChemRxiv, 2020, doi.org/10.26434/chemrxiv.11920947.v1. [link]

62. Deoxyfluorination using CuF2: Enabled by Using a Lewis Base Activating Group

D. E. Sood, S. Champion, D. M. Dawson, S. Chabbra, B. E. Bode, A. Sutherland, and A. J. B. Watson, Angew. Chem. Int. Ed. 2020, doi/10.1002/anie.202001015. [link]

  • Previously available as a preprint on ChemRxiv. [link]

61. Mechanistic Development and Recent Applications of the Chan–Lam Amination

M. J. West, J. W. B. Fyfe, J. C. Vantourout, and A. J. B. Watson, Chem. Rev. 2019, 11912491–12523. [pdf]

60. Discovery, scope, and limitations of an N‐dealkylation/N‐arylation of secondary sulfonamides under Chan–Lam conditions

M. J. West, B. Thomson, J. C. Vantourout, and A. J. B. Watson, Asian J. Org. Chem. 2020, 9, 364–367. [pdf]

59. Ni vs. Pd in Suzuki–Miyaura sp2–sp2 cross-coupling: a head-to-head study in a comparable precatalyst/ligand system

M. J. West, and A. J. B. Watson, Org. Biomol. Chem., 201917, 5055–5059. [pdf] [Supporting Information]

58. Mechanism of Cu-catalyzed Aryl Boronic Acid Halodeboronation Using Electrophilic Halogen: Development of a Base-Catalyzed Iododeboronation for Radiolabeling Applications

J. J. Molloy, K. M. O’Rourke, C. P. Frias, N. Sloan, M. J. West, S. L. Pimlott, A. Sutherland, and A. J. B. Watson, Org. Lett. 2019, 21, 2488−2492. [pdf] [Supporting Information]

57. N-Alkyl Amino Acids in Nature and their Biocatalytic Preparation

J. F. Hyslop, Sarah L. Lovelock, A. J. B. Watson, P. W. Sutton, G.-D. Roiban, J. Biotechnol. 2019, 293, 56–65. [pdf]

 

56. A Flow Platform for Degradation-free CuAAC Bioconjugation

M. Z. C. Hatit, L. F. Reichenbach, J. M. Tobin, F. Vilela, G. A. Burley, A. J. B. Watson, Nature Comm. 2018, 9, 4021. [link]

  • Highlighted in Nature Communications. [link]

55. A Cascade Suzuki-Miyaura/Diels-Alder Protocol: Exploring the Bifunctional Utility of Vinyl Bpin

D. L. Cain, C. McLaughlin, J. J. Molloy, C. Carpenter-Warren, N. A. Anderson, A. J. B. Watson, Synlett DOI: ST-2018-08-0509-L. [pdf]

  • Highlighted in Thieme. [link]

54. Mechanistic Insight Enables Practical, Scalable, Room Temperature Chan-Lam N-Arylation of N-Aryl Sulfonamides

J. C. Vantourout, L. Li, E. Bendito-Moll, S. Chabbra, K. Arrington, B. E. Bode, A. Isidro-Llobet, J. A. Kowalski, M. Nilson, K. Wheelhouse, J. L. Woodward, S. Xie, D. C. Leitch, and A. J. B. Watson, ACS Catalysis 2018, 8, 9560–9566. [pdf] [Supporting Information]

  • A most read paper in ACS Catalysis.

53. Dimethylisosorbide (DMI) as a Bioderived Solvent for Pd-Catalyzed Cross-coupling Reactions

K. L. Wilson, J. Murray, H. F. Sneddon, C. Jamieson, and A. J. B. Watson, Synlett DOI: ST-2018-08-0509-L. [pdf] [Supporting Information]

52. Biocatalytic Synthesis of Chiral N-Functionalized Aminoacids

J. F. Hyslop, S. L. Lovelock, P. W. Sutton, K. W. Brown, A. J. B. Watson, and G.-D. Roiban Angew. Chem. Int. Ed. DOI: 10.1002/anie.201806893. [pdf] [Supporting Information]

 

51. Catalytic Enantioselective Synthesis of Chiral Azahetrocyclic Ethylamines by Asymmetric Protonation

C. Xu, C. W. Muir, A. G. Leach, A. R. Kennedy, and A. J. B. Watson, Angew. Chem. Int. Ed. DOI: 10.1002/anie.201806956 [pdf] [Supporting Information]

50. Discovery of Tetrahydroquinoxalines as Bromodomain and Extra-Terminal Domain (BET) Inhibitors with Selectivity for the Second Bromodomain

R. P. Law, S. J. Atkinson, P. Bamborough, C. Chung, E. H Demont, L. J. Gordon, M. Lindon, R. K. Prinjha, A. J. B. Watson, and D. J. Hirst, J. Med. Chem. 2018, 61, 4317–4334. [pdf] [Supporting Information]

  • Highlighted in the Practical Fragments blog [link]

49.Cyrene as a Bio-based Solvent for HATU Mediated Amide Coupling

K. L. Wilson, J. Murray, C. Jamieson, and A. J. B. Watson, Org. Biomol. Chem. 2018, 16, 2851–2854. [pdf] [Supporting Information]

48. Scalable Total Synthesis and Comprehensive Structure–Activity Relationship Studies of the Phytotoxin Coronatine

J. B. Watson, Nat. Commun. DOI: 10.1038/s41467-018-03443-1. [pdf] [Supporting Information]

  • Highlighted in Nature Communications. [link]

47. Contra-Thermodynamic, Photocatalytic EZ Isomerization of Styrenyl Boron Species: Vectors to Facilitate Exploration of 2D Chemical Space

J. B. Metternich, C. G. Daniliuc, A. J. B. Watson, and R. Gilmour, Angew. Chem. Int. Ed. 2018, 57, 3168–3172. [pdf] [Supporting Information]

  • Highlighted in C&EN [link]

46. Interrogating Pd(II) Anion Metathesis using a Bifunctional Chemical Probe: A Transmetalation Switch

2018, 140, 126−130

  • Highlighted in SynFacts [link]

45. A Multi-component Route to Functionalized Amides and Oxazolidinones

44. Practical Synthesis of Pharmaceutically Relevant Molecules Enriched in sp3 Character

  • Highlighted in Chemistry World

43. Chemoselective One-pot Synthesis of Functionalized Amino-azaheterocycles Enabled by COware

42. Cyrene as a Bio-based Solvent for the Suzuki-Miyaura Cross-coupling

  • Highlighted in the ACS Nexus blog [link].

41. Connecting the Dots: Method Development Using Sustainable Solvents

40. A One-pot Tandem Chemoselective Allylation/Cross-coupling via Temperature Control of a Multi-nucleophile/electrophile System

39. Recent Developments in Organoboron Chemistry: Old Dogs, New Tricks

38. Modular, Step-efficient Palladium-catalyzed Cross-coupling Strategy to Access C6-Heteroaryl 2-Aminopurine Ribonucleosides

, , , and Org. Lett. 2017, 19, 3759-3762. [pdf] [Supporting Information]

37. A Strategy for Conditional Orthogonal CuAAC Reactions Using a Protected Aromatic Ynamine

, , , and J. Org. Chem. 2017, 82, 5461–5468. [pdf] [Supporting Information]

36. Amidation of Unactivated Ester Derivatives Mediated by Trifluoroethanol

C. G. McPherson, N. Caldwell, C. Jamieson, I. Simpson, and A. J. B. Watson Org. Biomol. Chem. 2017, 15, 3507–3518. [pdf] [Supporting Information]

35. Spectroscopic Studies of the Chan-Lam Amination: A Mechanism-inspired Solution to Boronic Ester Reactivity

J. C. Vantourout, H. N. Miras, A. Isidro-Llobet, S. Sproules, and A. J. B. Watson J. Am. Chem. Soc. 2017, 139, 4769–4779. [pdf] [Supporting Information]

  • Highlighted in Organic Chemistry Portal [link]
  • Highlighted by Derek Lowe [link]
  • Highlighted in OPRD
  • A most read paper in JACS

34. Rational Design of Autotaxin Inhibitors by Structural Evolution of Endogenous Modulators

W.-J. Keune, F. Potjewyd, T. Hediebrecht, F. Salgado-Polo, S. J. F. Macdonald, L. Chelvarajan, A. A. Latif, S. Soman, A. J. Morris, A. J. B. Watson, C. Jamieson, and A. Perrakis J. Med. Chem. 2017, 60, 2006–2017. [pdf] [Supporting Information]

33. Determining the Origin of Rate-independent Chemoselectivity in CuAAC Reaction: An Alkyne-specific Shift in Rate-determining Step

C. P. Seath, G. A. Burley, and A. J. B. Watson Angew. Chem. Int. Ed. 2017, 56, 3314–3318. [pdf] [Supporting Information]

32. The Emergence of Small Molecule Non-RGD-mimetic Inhibitors for RGD Integrins

L. M. Miller, J. Pritchard, S. J. F. Macdonald, C. Jamieson, and A. J. B. Watson J. Med. Chem. 2017, 60, 3241–3251.[pdf]

31. Structure-activity Relationships of Small Molecule Autotaxin Inhibitors with a Discrete Binding Mode

L. M. Miller, W.-J. Keune, D. Castagna, L. Young, E. Duffy, F. Potjewyd, F. Salgado-Polo, P. Engel García, D. Semaan, J. Pritchard, A. Perrakis, S. J. F. Macdonald, C. Jamieson, and A. J. B. Watson J. Med. Chem. 2017, 60, 722–748. [pdf] [Supporting Information]

30. Chemoselective Suzuki-Miyaura Cross-coupling via Kinetic Transmetallation

J. W. B. Fyfe, N. J. Fazakerley, and A. J. B. Watson Angew. Chem. Int. Ed. 2017, 56, 1249–1253. [pdf] [Supporting Information]

  • A most read article in ACIE during December 2016

29. Chemoselective Brown Oxidation of Aryl Organoboron Systems Enabled by Boronic Acid-selective Phase Transfer

J. J. Molloy, T. A. Clohessy, C. Irving, N. A. Anderson, G. C. Lloyd-Jones, and A. J. B. Watson Chem. Sci. 2017, 8, 1551–1559. [pdf] [Supporting Information]

  • Highlighted in OPRD

28. Scope and Limitations of a DMF Bio-alternative within Sonogashira Cross-coupling and Cacchi-type Annulation

K. L. Wilson, A. R. Kennedy, J. Murray, B. Greatrex, C. Jamieson, and A. J. B. Watson Beilstein J. Org. Chem. 2016, 12, 2005-2011. [pdf] [Supporting Information]

  • Highlighted in the ACS Nexus blog [link].

27. Synthesis of Oxindoles and Benzofuranones via Oxidation of 2-Heterocyclic BMIDAs

C. P. Seath, J. W. B. Fyfe, J. J. Molloy, and A. J. B. Watson Synthesis 2017, 49, 891–898. [pdf] [Supporting Information]

26. Highlights from the 51st EUCHEM Conference on Stereochemistry, Bürgenstock, Switzerland, May 2016

A. J. B. Watson and J. R. Frost Chem. Commun. 2016, 52, 9173–9177. [pdf]

 

25. Synthesis of 2-BMIDA 6,5-Bicyclic Heterocycles by Cu(I)/Pd(0)/Cu(II) Cascade Catalysis of 2-Iodoanilines/phenols

C. P. Seath, K. L. Wilson, A. Campbell, J. M. Mowat, and A. J. B. Watson, Chem. Commun. 2016, 52, 8703–8706. [pdf] [Supporting Information]

24. Synthetic Approaches to Coronafacic Acid, Coronamic Acid, and Coronatine

M. M. Littleson, C. J. Russell, E. C. Frye, K. B. Ling, C. Jamieson, and A. J. B. Watson, Synthesis, 2016, 48, 3429–3448. [pdf]

23. GSK6853, a Chemical Probe for Inhibition of the BRPF1 Bromodomain

P. Bamborough, H. A. Barnett, I. Becher, M. J. Bird, C. Chung, P. D. Craggs, E. H. Demont, H. Diallo, D. J. Fallon, L. J. Gordon, P. Grandi, C. I. Hobbs, E. Hooper-Greenhill, E. J. Jones, R. P. Law, A. Le Gall, D. Lugo, A.-M. Michon, D. J. Mitchell, R. K. Prinjha, R. J. Sheppard, A. J. B. Watson, and R. J. Watson, ACS Med. Chem. Lett. 2016, 7, 552–557. [pdf] [Supporting Information]

  • Selected as an ACS Editor’s Choice Article
  • A Most Read Paper in ACS Med. Chem. Lett. in 2016

22. Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem

J. C. Vantourout, R. P. Law, A. Isidro-Llobet, S. J. Atkinson, and A. J. B. Watson, J. Org. Chem. 2016, 81, 3942–3950. [pdf] [Supporting Information]

  • Top 5 Most Read Article (April-May 2016)
  • Highlighted in OPRD
  • A Most Read Paper in J. Org. Chem. in 2016
  • Highlighted in Organic Chemistry Portal [link]

21. Chemoselective Sequential Click Ligations Directed by Enhanced Reactivity of an Aromatic Ynamine

M. Z. C. Hatit, J. C. Sadler, L. A. McLean, B. C. Whitehurst, C. P. Seath, L. D. Humphreys, R. J. Young, A. J. B. Watson, and G. A. Burley, Org. Lett. 2016, 18, 1694–1697. [pdf] [Supporting Information]

20. The Development of Autotaxin Inhibitors: An Overview of the Patent and Primary Literature

D. Castagna, D. C. Budd, S. J. F. Macdonald, C. Jamieson, and A. J. B. Watson, J. Med. Chem. 2016, 59, 5604–5621. [pdf]

 

19. When Two Reactions Become One

J. W. B. Fyfe and A. J. B. Watson, Science 2016, 351, 26–27. [pdf] See the original article by Prof Jim Morken here.

  • Highlighted in C&EN.

 

18. One-Pot Homologation of Boronic Acids: A Platform for Diversity-Oriented Synthesis

C. W. Muir, J. C. Vantourout, A. Isidro-Llobet, S. J. F. Macdonald and A. J. B. Watson, Org. Lett. 2015, 17, 6030–6033. [pdf] [Supporting Information]

17. Tandem Chemoselective Suzuki-Miyaura Cross-coupling Enabled by Nucleophile Speciation Control

C. P. Seath, J. W. B. Fyfe, J. J. Molloy, and A. J. B. Watson, Angew. Chem. Int. Ed. 2015, 54, 9976–9979. [pdf] [Supporting Information]

  • Highlighted in Science [link]
  • Highlighted in SynFACTS [link]

 

16. Development of Solvent Selection Guides

H. E. Eastman, C. Jamieson, and A. J. B. Watson, Aldrichimica Acta, 2015, 48, 51-55.

15. Catalytic Amidation of Unactivated Ester Derivatives Mediated by Trifluoroethanol

N. Caldwell, C. Jamieson, I. Simpson, and A. J. B. Watson, Chem. Commun., 2015, 51, 9495–9498. [pdf] [Supporting Information]

14. Identification of a Novel Class of Autotaxin Inhibitors Through Cross-screening

D. Castagna, E. L. Duffy, D. Semann, L. C. Young, J. M. Pritchard, S. J. F. MacDonald, D. C. Budd, C. Jamieson, and A. J. B. Watson, Med. Chem. Commun., 2015, 6, 1149-1155. [pdf] [Supporting Information]

13. Speciation Control During Suzuki-Miyaura Cross-coupling of Haloaryl and Haloalkenyl MIDA Boronic Ester

J. W. B. Fyfe, E. Valverde, C. P. Seath, A. R. Kennedy, J. M. Redmond, N. A. Anderson, and A. J. B. Watson, Chem.-Eur. J., 2015, 24, 8951–8964. [pdf] [Supporting Information]

12. Strategies Towards Chemoselective Suzuki-Miyaura Cross-Coupling

J. W. B. Fyfe  and A. J. B. Watson, Synlett (SynPACT), 2015, 26, 1139–1144. [pdf]

11. A Modular Synthesis of Functionalised Phenols Enabled by Controlled Boron Speciation

J. J. Molloy, R. P. Law, J. W. B. Fyfe, C. P. Seath, D. J. Hirst, and A. J. B. Watson, Org. Biomol. Chem.2015, 13, 3093-3102. [pdf] [Supporting Information]

10. Chemoselective Boronic Ester Synthesis by Controlled Speciation

J. W. B. Fyfe, C. P. Seath, and A. J. B. Watson, Angew. Chem. Int. Ed.2014, 53, 12077-12080. [pdf] [Supporting Information]

9. Amidation of Esters with Amino Alcohols Using Organobase Catalysis

N. Caldwell, P. S. Campbell, C. Jamieson, F. Potjewyd,  I. Simpson, and A. J. B. Watson, J. Org. Chem., 2014, 79, 9347-9354. [pdf] [Supporting Information]

8. Molar Efficiency: A Useful Metric to Gauge Relative Reaction Efficiency in Discovery Medicinal Chemistry

F. I. McGonagle, H. F. Sneddon, C. Jamieson, and A. J. B. Watson, ACS Sustainable Chem. Eng., 2014, 2, 523-532. [pdf] [Supporting Information]

MolEFigure

7. Synthesis of Functionalised 4H-Quinolizinones via Tandem Horner-Wadsworth-Emmons Olefination/Cyclisation

C. W. Muir, A. R. Kennedy, J. M. Redmond, and A. J. B. Watson, Org. Biomol. Chem., 2013, 11, 3337-3340. [pdf] [Supporting Information]

6. Development of a Solvent Selection Guide for Aldehyde-based Direct Reductive Amination Processes

F. I. McGonagle, D. S. MacMillan, J. Murray, H. F. Sneddon, C. Jamieson, and A. J. B. Watson, Green Chem., 2013, 15, 1159-1165. [pdf] [Supporting Information]

 

5. Development of a Catalytic Ester Amidation Process

N. Caldwell, C. Jamieson, I. Simpson, and A. J. B. Watson, ACS Sustainable Chem. Eng., 2013, 1, 1339-1344. [pdf] [Supporting Information]

 

4. Evaluation of Alternative Solvents in Common Amide Coupling Reactions:Replacement of Dichloromethane and N,N-Dimethylformamide

D. S. MacMillan, J. Murray, H. F. Sneddon, C. Jamieson, and A. J. B. Watson, Green Chem., 2013, 15, 596-600. [pdf] [Supporting Information]

 

3. Soft Scorpionates as Platforms for Novel Heterocycles

R. Rajasekharan Nair, A. Marckwordt, S. Lutta, M. Schwalbe, A. Biernat, D. R. Armstrong, A. J. B. Watson, A. R. Kennedy, J. Reglinski, and M. D. Spicer, Chem.-Eur. J., 2013, 19, 13561–13568. [pdf] [Supporting Information]

 

2. Replacement of Dichloromethane Within Chromatographic Purification: A Guide to Alternative Solvents

D. S. MacMillan, J. Murray, H. F. Sneddon, C. Jamieson, and A. J. B. Watson, Green Chem., 2012, 14, 3016-3019. [pdf] [Supporting Information]

 

1. Asymmetric Rhodium-Catalysed Addition of Arylboronic Acids to Acyclic Unsaturated Esters Containing a Basic delta-Amino Group.

N. A. Anderson, B. J. Fallon, E. Valverde, S. J. F. MacDonald, J. M. Pritchard, C. J. Suckling, and A. J. B. Watson, Synlett, 2012, 2817-2821. [pdf]

Publications from PhD studies

7. Development of chiral heteroleptic magnesium amides; asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates

E. L. Carswell, William J. Kerr, Duncan McArthur, Marek Pazicky, A. J. B. Watson, Tetrahedron, 2014, 70, 7344-7349. [pdf]

 

6. Towards Energetically Viable Asymmetric Deprotonations: Selectivity at More Elevated Temperatures with C2-Symmetric Magnesium Bisamides

L. S. Bennie, W. J. Kerr, M. Middleditch, and A. J. B. Watson, Chem. Commun., 2011, 47, 2264-2266. [pdf] [Supporting Information]

 

5. New Potentially Chelating Chiral Magnesium Amide Bases for Use in Enantioselective Deprotontion Reactions

W. J. Kerr, M. Middleditch, and A. J. B. Watson, Synlett, 2011, 177-180. [pdf]

 

4. Tuned methods for conjugate addition to a vinyl oxadiazole: synthesis of pharmaceutically important motifs

A. R. Burns, J. H. Kerr, W. J. Kerr, J. Passmore, L. C. Paterson, and A. J. B. Watson, Org. Biomol. Chem., 2010, 8, 2777-2783. [pdf] [Supporting Information]

 

3. Di-tert-Butylmagnesium as an Atom-efficient, Carbon-centred Base Reagent for the Preparation of Silyl Enol Ethers from Ketones

W. J. Kerr, A. J. B. Watson, and D. Hayes, Synlett, 2008, 1386-1390. [pdf]

 

2. In situ Generation of Mes2Mg as a Non-nucleophilic Carbon-centred Base Reagent for the Efficient One-pot Conversion of Ketones to Silyl Enol Ethers

W. J. Kerr, A. J. B. Watson, and D. Hayes, Org. Biomol. Chem., 2008, 6, 1238-1243. [pdf]

 

1. Bismesitylmagnesium: A Thermally Stable and Non-nucleophilic Carbon-centred Base Reagent for the Efficient Preparation of Silyl Enol Ethers

W. J. Kerr, A. J. B. Watson, and D. Hayes, Chem. Commun., 2007, 5049-5051. [pdf] [Supporting Information]

 

Book chapters

6. J. C. Vantourout, A. Isidro-Llobet, and A. J. B. Watson, “Conventional and Bio-inspired Syntheses of Monoterpene Indole Alkaloids” in Studies in Natural Product Chemistry, vol. 55: Atta-ur-Rahman, Ed., Elsevier, Chapter 1.

5. J. J. Molloy and A. J. B. Watson, “B-Protected Boronic Acids” in Boron Reagents in Synthesis (ACS Symposium Series): A. Coca, Ed., ACS, Chapter 12, pp 379–413 (DOI: 10.1021/bk-2016-1236.ch012).

4. C. Jamieson and A. J. B. Watson, “Application of Organocatalysis in Sustainable Synthesis” In Catalysis for Sustainability: Goals, Challenges, and Impacts: T. A. Umile, Ed., Taylor and Francis, Chapter 3, p 47–82.

3. A. J. B. Watson and D. W. C. MacMillan, “Iminium Catalysis” In Science of Synthesis Reference Library: Asymmetric Organocatalysis: B. List, Ed., Chapter 1.1.7, p 309–401.

2. A. J. B. Watson and D. W. C. MacMillan, “alpha-Functionalisation of Carbonyl Compounds (Not Enolate)” In Science of Synthesis: Stereoselective Synthesis 3: Stereoselective Pericyclic Reactions, Cross Coupling, and C-H and C-X Activation: P. A. Evans, Ed., Chapter 3.16, p 675–745.

1. A. J. B. Watson and D. W. C. MacMillan, “Iminium and Enamine Catalysis” In Catalytic Asymmetric Synthesis, 3rd ed.; I. Ojima, Ed., Chapter 2, p 39–57.