Dr Louis Morrill
Senior Lecturer in Synthetic Organic Chemistry
Overview
Research in the Morrill group is focused on inventing new reactions in organic chemistry and developing sustainable catalytic methodologies for synthesis. The utility and impact of our research will ultimately be exemplified through its application in the total synthesis of natural products and molecules of biological significance.
Current core areas of interest include:
- Borrowing hydrogen (also called hydrogen auto transfer) catalysis
- Synthetic organic electrochemistry
- Frustrated Lewis Pair (FLP) catalysis (in collaboration with Dr Rebecca Melen)
- Exploring new synthetic routes towards cyanamides (in collaboration with Syngenta)
These projects will serve as an excellent platform for talented and highly motivated students to receive a first-class training in synthetic organic chemistry that will thoroughly prepare them for a future career in the chemical industry or in academia.
We are also actively engaged in a number of collaborative research projects in the following areas:
- Employing enabling tools (flow and mechanochemistry) for organocatalysis (collaboration led by Dr Duncan Browne)
- Organocatalytic artificial enzymes (collaboration led by Dr Louis Luk)
Please see also:
Biography
Louis was born in Wick on the north coast of Scotland and obtained his MChem degree (1st Class Honours) from the University of St Andrews, including a one-year industrial placement at AstraZeneca (Charnwood). He completed his Masters research project in 2010 with Professor Andrew Smith.
Staying at St Andrews, he completed his Ph.D. under the direction of Professor Andrew Smith entitled "Organocatalytic Functionalisation of Carboxylic Acids Using Isothioureas", funded by a prestigious Carnegie-Caledonian Scholarship (2010-2014). This work expanded the utility of isothioureas in Lewis base catalysis and demonstrated the first intermolecular bond-forming reaction of carboxylic acid-derived ammonium enolates
For his postdoctoral research, he moved to UC Berkeley to join the research group of Professor Richmond Sarpong, entering the world of complex molecule synthesis. Specifically, he was part of a team that developed highly efficient and concise total syntheses of diterpenoid alkaloid natural products. In 2015, he was appointed as a University Research Fellow in Synthetic Organic Chemistry at Cardiff University and began his independent research career.
Publications
2023
- El Gehani, A. A. M. A., Maashi, H. A., Harnedy, J. and Morrill, L. C. 2023. Electrochemical generation and utilization of alkoxy radicals. Chemical Communications (10.1039/d3cc00302g)
- Harnedy, J., Maashi, H. A., El Gehani, A. A. M. A., Burns, M. and Morrill, L. C. 2023. Deconstructive functionalization of unstrained cycloalkanols via electrochemically generated aromatic radical cations. Organic Letters 25(9), pp. 1486-1490. (10.1021/acs.orglett.3c00219)
2022
- Kustiana, B. A., Melen, R. L. and Morrill, L. C. 2022. One-pot synthesis of styrene derivatives from allyl silanes via b(c6f5)3-catalyzed isomerization-Hiyama coupling. Organic Letters 24(47), pp. 8694-8697. (10.1021/acs.orglett.2c03584)
- Jones, A. C., Williams, M. T. J., Morrill, L. C. and Browne, D. L. 2022. Mechanical activation of zero-valent metal reductants for nickel-catalyzed cross-electrophile coupling. ACS Catalysis 12(21), pp. 13681-13689. (10.1021/acscatal.2c03117)
- Kustiana, B. A., Elsherbeni, S. A., Linford‐Wood, T. G., Melen, R. L., Grayson, M. N. and Morrill, L. C. 2022. B(C 6 F 5 ) 3 ‐Catalyzed E ‐selective isomerization of alkenes. Chemistry - A European Journal, article number: e202202454. (10.1002/chem.202202454)
- Seastram, A. C., Hareram, M. D., Knight, T. M. B. and Morrill, L. C. 2022. Electrochemical alkene azidocyanation via 1,4-nitrile migration. Chemical Communications 58, pp. 8658-8661. (10.1039/D2CC02958H)
- Hareram, M. D. et al. 2022. Electrochemical deconstructive functionalization of cycloalkanols via alkoxy radicals enabled by proton-coupled Electron transfer. Organic Letters 24(21), pp. 3890-3895. (10.1021/acs.orglett.2c01552)
- Williams, M. T. J., Morrill, L. C. and Browne, D. L. 2022. Mechanochemical organocatalysis: do high enantioselectivities contradict what we might expect?. ChemSusChem 15(2), article number: e202102157. (10.1002/cssc.202102157)
2021
- Nodling, A. R. et al. 2021. The role of protein environment in catalysis by biotinylated secondary amines. Organic and Biomolecular Chemistry 19, pp. 10424-10431. (10.1039/D1OB01947C)
- Harnedy, J., Hareram, M. D., Tizzard, G. J., Coles, S. J. and Morrill, L. C. 2021. Electrochemical oxidative Z-selective C(sp2)-H chlorination of acrylamides. Chemical Communications 57(94), pp. 12643-12646. (10.1039/D1CC05824J)
- Nicholson, W. I. et al. 2021. Ball-milling-enabled reactivity of manganese metal. Angewandte Chemie International Edition 60(43), pp. 23128-23133. (10.1002/anie.202108752)
- Reed-Berendt, B. G., Latham, D. E., Dambatta, M. B. and Morrill, L. C. 2021. Borrowing hydrogen for organic synthesis. ACS Central Science 7(4), pp. 570-585. (10.1021/acscentsci.1c00125)
- Basak, S., Winfrey, L., Kustiana, B. A., Melen, R. L., Morrill, L. C. and Pulis, A. P. 2021. Electron deficient borane-mediated hydride abstraction in amines: stoichiometric and catalytic processes. Chemical Society Reviews 50(6), pp. 3721-3737. (10.1039/D0CS00531B)
- Santi, N., Morrill, L. C., Swiderek, K., Moliner, V. and Luk, L. Y. P. 2021. Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalyst. Chemical Communications 57(15), pp. 1919-1922. (10.1039/D0CC08142F)
2020
- Williams, M. T. J., Morrill, L. C. and Browne, D. L. 2020. Expedient organocatalytic Aza-Morita–Baylis–Hillman reaction through ball-milling. ACS Sustainable Chemistry and Engineering 8(48), pp. 17876-17881. (10.1021/acssuschemeng.0c07320)
- Dambatta, M. B., Santos, J., Bolt, R. and Morrill, L. C. 2020. Transition metal free α-C-alkylation of ketones using secondary alcohols. Tetrahedron 76(45), article number: 131571. (10.1016/j.tet.2020.131571)
- Santi, N., Morrill, L. C. and Luk, L. Y. P. 2020. Streptavidin-hosted organocatalytic aldol addition. Molecules 25(10), article number: 2457. (10.3390/molecules25102457)
- Basak, S., Alvarez-Montoya, A., Winfrey, L., Melen, R. L., Morrill, L. C. and Pulis, A. P. 2020. B(C6F5)3-catalyzed direct C3 alkylation of indoles and oxindoles. ACS Catalysis 10(8), pp. 4835-4840. (10.1021/acscatal.0c01141)
- Reed-Berendt, B. G., Mast, N. and Morrill, L. C. 2020. Manganese-catalyzed one-pot conversion of nitroarenes into N-methylarylamines uising methanol. European Journal of Organic Chemistry 2020(9), pp. 1136-1140. (10.1002/ejoc.201901854)
- Nicholson, W. I., Seastram, A. C., Iqbal, S. A., Reed-Berendt, B. G., Morrill, L. C. and Browne, D. L. 2020. N-Heterocyclic carbene acyl anion organocatalysis by ball-milling. ChemSusChem 13(1), pp. 131-135. (10.1002/cssc.201902346)
2019
- Allen, B. D. W., Mishra, D., Seastram, A. C., McBride, T., Wirth, T., Browne, D. L. and Morrill, L. C. 2019. Manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols via alkoxy radicals. Organic Letters 21(22), pp. 9241-9246. (10.1021/acs.orglett.9b03652)
- Latham, D. E., Polidano, K., Williams, J. M. J. and Morrill, L. C. 2019. One-pot conversion of allylic alcohols to α-methyl ketones via iron-catalyzed isomerization-methylation. Organic Letters 21(19), pp. 7914-7918. (10.1021/acs.orglett.9b02900)
- Polidano, K., Williams, J. M. J. and Morrill, L. C. 2019. Iron-catalyzed borrowing hydrogen β-C(sp3)-methylation of alcohols. ACS Catalysis 9(9), pp. 8575-8580. (10.1021/acscatal.9b02461)
- Dambatta, M., Polidano, K., Northey, A. D., Williams, J. M. J. and Morrill, L. C. 2019. Iron‐catalyzed borrowing hydrogen C‐Alkylation of oxindoles with alcohols. ChemSusChem 12(11), pp. 2345-2349. (10.1002/cssc.201900799)
- Reed-Berendt, B. G., Polidano, K. and Morrill, L. C. 2019. Recent advances in homogeneous borrowing hydrogen catalysis using earth-abundant first row transition metals. Organic and Biomolecular Chemistry 17(7), pp. 1595-1607. (10.1039/C8OB01895B)
- Reed-Berendt, B. G. and Morrill, L. C. 2019. Manganese-catalyzed N-alkylation of sulfonamides using alcohols. Journal of Organic Chemistry 84(6), pp. 3715-3724. (10.1021/acs.joc.9b00203)
2018
- Nodling, A. R. et al. 2018. Reactivity and selectivity of iminium organocatalysis improved by a protein host. Angewandte Chemie International Edition 57(38), pp. 12478-12482. (10.1002/anie.201806850)
- Khan, I., Reed-Berendt, B. G., Melen, R. L. and Morrill, L. C. 2018. FLP-catalyzed transfer hydrogenation of silyl enol ethers. Angewandte Chemie International Edition 57(38), pp. 12356-12359. (10.1002/anie.201808800)
- Ayres, J. N., Williams, M., Tizzard, G. J., Coles, S. J., Ling, K. B. and Morrill, L. C. 2018. Synthesis and reactivity of N-allenyl cyanamides. Organic Letters 20(17), pp. 5282-5285. (10.1021/acs.orglett.8b02225)
- Polidano, K., Allen, B. D. W., Williams, J. M. J. and Morrill, L. C. 2018. Iron-catalyzed methylation using the borrowing hydrogen approach. ACS Catalysis 8, pp. 6440-6445. (10.1021/acscatal.8b02158)
- Kou, K. G. M. et al. 2018. A benzyne insertion approach to hetisine-type diterpenoid alkaloids: synthesis of cossonidine (davisine). Journal of the American Chemical Society 140(26), pp. 8105-8109. (10.1021/jacs.8b05043)
2017
- Polidano, K., Reed-Berendt, B., Basset, A., Watson, A., Williams, J. M. J. and Morrill, L. 2017. Exploring tandem ruthenium-catalyzed hydrogen transfer and SNAr chemistry. Organic Letters 19(24), pp. 6716-6719. (10.1021/acs.orglett.7b03441)
- Khan, I., Manzotti, M., Tizzard, G. J., Coles, S. J., Melen, R. L. and Morrill, L. C. 2017. Frustrated Lewis pair (FLP)-catalyzed hydrogenation of aza-Morita–Baylis–Hillman adducts and sequential organo-FLP catalysis. ACS Catalysis 7(11), pp. 7748-7752. (10.1021/acscatal.7b03077)
- Pflueger, J. J., Morrill, L. C., deGruyter, J. N., Perea, M. A. and Sarpong, R. 2017. Magnesiate addition/ring-expansion strategy to access the 6-7-6 tricyclic core of hetisine-type C20-diterpenoid alkaloids. Organic Letters 19(17), pp. 4632-4635. (10.1021/acs.orglett.7b02260)
- Ayres, J., Ashford, M., Stockl, Y., Prudhomme, V., Ling, K. B., Platts, J. and Morrill, L. 2017. Deoxycyanamidation of alcohols with N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS). Organic Letters 19(14), pp. 3835-3838. (10.1021/acs.orglett.7b01710)
2016
- Ayres, J., Ling, K. B. and Morrill, L. 2016. N-Cyanation of secondary amines using Trichloroacetonitrile. Organic Letters 18(21), pp. 5528-5531. (10.1021/acs.orglett.6b02775)
- Van, K. N., Morrill, L., Smith, A. D. and Romo, D. 2016. Catalytic generation of ammonium enolates and related tertiary amine-derived intermediates: applications, mechanism and stereochemical models (n→π*). In: Vedejs, E. and Denmark, S. E. eds. Lewis Base Catalysis in Organic Synthesis. Wiley, pp. 527-654., (10.1002/9783527675142.ch13)
- Smith, A. D., Stark, D., Morrill, L., Cordes, D., Slawin, A. and O'Riordan, T. 2016. Enantioselective synthesis of 3,5,6-substituted dihydropyranones and dihydropyridinones using isothiourea-mediated catalysis. Chemistry - An Asian Journal 11(3), pp. 395-400. (10.1002/asia.201500907)
2015
- Smith, S. R. et al. 2015. Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines. Chemistry - A European Journal 21(29), pp. 10530-10536. (10.1002/chem.201501271)
- Millet, A., Baudoin, O. and Morrill, L. 2015. Palladium-catalyzed β -Selective C(sp3)-H Arylation of N-Boc-Piperidines. Organic Syntheses 92, pp. 76-90. (10.15227/orgsyn.092.0076)
- Campbell, C. D., Joannesse, C., Morrill, L., Philp, D. and Smith, A. D. 2015. Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates. Organic & Biomolecular Chemistry 13(10), pp. 2895-2900. (10.1039/C4OB02629B)
- Morrill, L. et al. 2015. Isothiourea-catalyzed Michael Addition to unsaturated trichloromethyl ketones. Synfacts 11(3), article number: 315. (10.1055/s-0034-1380058)
2014
- Morrill, L. et al. 2014. Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents. Organic & Biomolecular Chemistry 12(44), pp. 9016-9027. (10.1039/C4OB01788A)
- Morrill, L. and Smith, A. D. 2014. Organocatalytic Lewis base functionalisation of carboxylic acids, esters and anhydrides via C1-ammonium or azolium enolates. Chemical Society Reviews 43(17), pp. 6214-6226. (10.1039/C4CS00042K)
- De Savi, C. et al. 2014. Efficacious inhaled PDE4 inhibitors with low emetic potential and long duration of action for the treatment of COPD. Journal of Medicinal Chemistry 57(11), pp. 4661-4676. (10.1021/jm5001216)
- Morrill, L. C., Smith, S. M., Slawin, A. M. Z. and Smith, A. D. 2014. Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids. Journal of Organic Chemistry 79(4), pp. 1640-1655. (10.1021/jo402591v)
- Smith, A. D., Douglas, J., Morrill, L. C. and Richmond, E. 2014. Lewis base catalyzed asymmetric formal [2+2] cycloadditions. In: Nishiwaki, N. ed. Methods and Applications of Cycloaddition Reactions in Organic Syntheses. Wiley, pp. 89-114., (10.1002/9781118778173.ch03)
- Morrill, L., Ledingham, L. A., Couturier, J., Bickel, J., Harper, A. D., Fallan, C. and Smith, A. D. 2014. 2-Arylacetic anhydrides as ammonium enolate precursors. Organic & Biomolecular Chemistry 12(4), pp. 624-636. (10.1039/C3OB41869C)
2013
- Stark, D. G., Morrill, L., Yeh, P., Slawin, A. M. Z., O'Riordan, T. J. C. and Smith, A. D. 2013. Isothiourea-mediated one-pot synthesis of functionalized pyridines. Angewandte Chemie - International Edition 52(44), pp. 11642-11646. (10.1002/anie.201306786)
- Davies, A. T. et al. 2013. Stereospecific Asymmetric N-Heterocyclic Carbene (NHC)-Catalyzed Redox Synthesis of Trifluoromethyl Dihydropyranones and Mechanistic Insights. Journal of Organic Chemistry 78(18), pp. 9243-9257. (10.1021/jo401433q)
- Morrill, L., Douglas, J., Lebl, T., Slawin, A. M. Z., Fox, D. J. and Smith, A. D. 2013. Isothiourea-mediated asymmetric Michael-lactonisation of trifluoromethylenones: a synthetic and mechanistic study. Chemical Science 4(11), pp. 4146-4155. (10.1039/c3sc51791h)
- Stark, D. G., Morrill, L., Yeh, P. -., Slawin, A. M., O’Riordan, T. J. and Smith, A. D. 2013. Isothiourea-catalyzed pyridine synthesis. Synfacts 9(12), article number: 1344. (10.1055/s-0033-1340279)
2012
- Morrill, L., Lebl, T., Slawin, A. M. Z. and Smith, A. D. 2012. Catalytic asymmetric α-amination of carboxylic acids using isothioureas. Chemical Science 3(6), pp. 2088-2093. (10.1039/c2sc20171b)
- Joannesse, C. et al. 2012. Isothiourea-mediated asymmetric O- to C-carboxyl transfer of oxazolyl carbonates: structure-selectivity profiles and mechanistic studies. Chemistry - a European Journal 18(8), pp. 2398-2408. (10.1002/chem.201102847)
2011
- Woods, P. A., Morrill, L., Bragg, R. A. and Smith, A. D. 2011. Isothiourea-catalysed asymmetric C-acylation of silyl ketene acetals. Chemistry - a European Journal 17(39), pp. 11060-11067. (10.1002/chem.201100995)
- Belmessieri, D., Morrill, L., Simal, C., Slawin, A. M. Z. and Smith, A. D. 2011. Organocatalytic functionalization of carboxylic acids: isothiourea-catalyzed asymmetric intra- and intermolecular Michael Addition−lactonizations. Journal of the American Chemical Society 133(8), pp. 2714-2720. (10.1021/ja109975c)
- Smith, A., Joannesse, C., Morrill, L., Campbell, C. and Slawin, A. 2011. Isothiourea-catalyzed asymmetric O- to C-carboxyl transfer of furanyl carbonates. Synthesis (Stuttgart) 2011(12), pp. 1865-1879. (10.1055/s-0030-1260602)
- Belmessieri, D., Morrill, L., Simal, C., Slawin, A. M. Z. and Smith, A. D. 2011. Asymmetric Michael Addition-Lactonization of Carboxylic Acids. Synfacts 2011(4), pp. 436. (10.1055/s-0030-1259622)
2010
- Aitken, R. A., Cleghorn, L. P., Leitch, R. M., Morrill, L. and Slawin, A. M. Z. 2010. Unexpected rearrangement leading to formation of a 1,3-Bis(triphenylphosphonio)prop-1-en-3-idyl carboxylate. European Journal of Organic Chemistry 2010(17), pp. 3211-3214. (10.1002/ejoc.201000143)
- Woods, P. A., Morrill, L., Lebl, T., Slawin, A. M. Z., Bragg, R. A. and Smith, A. D. 2010. Isothiourea-mediated stereoselectiveC-acylation of silyl ketene acetals. Organic Letters 12(11), pp. 2660-2663. (10.1021/ol1008747)
2008
- Smith, A. et al. 2008. N-heterocyclic carbene catalysed oxygen-to-carbon carboxyl transfer of indolyl and benzofuranyl carbonates. Synthesis (Stuttgart) 2008(17), pp. 2805-2818. (10.1055/s-2008-1077890)
Teaching
Lecturer on the following courses:
CH4103 Foundations of Organic and Biological Chemistry (*New Course*)
CH3404 Asymmetric Synthesis of Pharmaceuticals and Natural Products - Organocatalysis (*New Course*)
CHT402 Recent Advances in Homogeneous Catalysis - Organocatalysis CDT Workshop (*New Course*)
Leading tutorials on the following courses:
CH4103 Foundations of Organic and Biological Chemistry
CH3104 Introduction to the Solid State & Applications of Spectroscopy
CH3105 Techniques and Methods in Chemistry
CH3202 Applications of Molecular Spectroscopy
CH3203 Organic Chemistry of Multiply Bonded Systems
CH3303 Advanced Organic Chemistry
Project supervisor for the following options:
CH3325 Final Year B.Sc. project
CH3401 Final Year MChem project
Research in the Morrill group is focused on inventing new reactions in organic chemistry and developing sustainable catalytic methodologies for synthesis. The utility and impact of our research will ultimately be exemplified through its application in the total synthesis of natural products and molecules of biological significance.
Current core areas of interest include:
- Borrowing hydrogen (also called hydrogen auto transfer) catalysis
- Synthetic organic electrochemistry
- Frustrated Lewis Pair (FLP) catalysis (in collaboration with Dr Rebecca Melen)
- Exploring new synthetic routes towards cyanamides (in collaboration with Syngenta)
These projects will serve as an excellent platform for talented and highly motivated students to receive a first-class training in synthetic organic chemistry that will thoroughly prepare them for a future career in the chemical industry or in academia.
We are also actively engaged in a number of collaborative research projects in the following areas:
- Employing enabling tools (flow and mechanochemistry) for organocatalysis (collaboration led by Dr Duncan Browne)
- Organocatalytic artificial enzymes (collaboration led by Dr Louis Luk)