Publications | MorrillGroup

Independent and Collaborative Publications:

(65)

Electrochemical Synthesis of C(sp3)-Rich Heterocycles via Mesolytic Cleavage of Anodically Generated Aromatic Radical Cations

H. A. Maashi, A. H. Husayni, K. M, M. E. Reid, J. Harnedy, E. C. Herneman, M. Pera-Titus and L. C. Morrill,* Org. Lett., 2024, DOI: 10.1021/acs.orglett.4c03091

(64)

Iron-Catalyzed Transfer Hydrogenation of Allylic Alcohols with Isopropanol

Md Abdul Bari, S. A. Elsherbeni, T. Maqbool, D. E. Latham, E. B. Gushlow, E. J. Harper and L. C. Morrill,* J. Org. Chem., 2024, 89, 14571-14576.

(63)

Electrochemical Deconstructive Methoxylation of Arylalcohols – A Synthetic and Mechanistic Investigation

H. A. Maashi, T. Lewis-Atwell, J. Harnedy, M. N. Grayson* and L. C. Morrill,* Chem. Eur. J., 2024, e20240341.

(62)

Electrochemical deconstructive functionalization of arylcycloalkanes via fragmentation of anodically generated aromatic radical cations

H. A. Maashi, A. H. Husayni, J. Harnedy and L. C. Morrill,* Chem. Commun., 2024, 60, 11190-11201. [Invited contribution to the ChemComm 60th Anniversary Collection]

(61)

Accessing Highly Substituted Indoles via B(C6F5)3-Catalyzed Secondary Alkyl Group Transfer

S. A. Elsherbeni, R. L. Melen,* A. P. Pulis* and L. C. Morrill*, J. Org. Chem., 2024, 89, 4244-4248.

(60)

Recent Advances in Catalysis using Organoborane Mediated Hydride Abstraction

J. P. Gillions, S. A. Elsherbeni, L. Winfrey, L. Yun, R. L. Melen*, L. C. Morrill* and A. P. Pulis*, Synlett, 2023, 34, 2117-2128. [Invited contribution to celebrate the 60th anniversary of the Matteson homologation] [Highlighted in the 14th EuCheMS Young Investigators Workshop Special Issue]

(59)

Nickel-Catalyzed Intramolecular Alkene Difunctionalization by Ball-Milling

M. T. J. Williams, L. C. Morrill* and D. L. Browne*, Adv. Synth. Catal., 2023, 365, 1477-1484. [Hot Topic: Earth-Abundant Transition Metal Catalysis]

(58)

Electrochemical Generation and Utilization of Alkoxy Radicals

A. A. M. A. El Gehani, H. A. Maashi, J. Harnedy and L. C. Morrill*, Chem. Commun., 2023, 59, 3655-3664. [Part of themed collection: Chemical Communications Hot Articles 2023]

(57)

Deconstructive Functionalization of Unstrained Cycloalkanols via Electrochemically-Generated Aromatic Radical Cations

J. Harnedy, H. A. Maashi, A. A. M. A. El Gehani, M. Burns and L. C. Morrill*, Org. Lett., 2023, 25, 1486-1490.

(56)

One-Pot Synthesis of Styrene Derivaties from Allyl Silanes via B(C6F5)3-Catalyzed Isomerization – Hiyama Coupling

B. A. Kustiana, R. L. Melen, and L. C. Morrill*, Org. Lett., 2022, 24, 8694-8697. [Highlighted in Chemistry Views] [Highlighted in Organic Chemistry Portal]

(55)

Mechanical Activation of Zero-Valent Metal Reductants for Nickel-Catalyzed Cross-Electrophile Coupling

A. C. Jones†, M. T. J. Williams†, L. C. Morrill*, and D. L. Browne*, ACS Catal., 2022, 12, 13681-13689.

(54)

B(C6F5)3-Catalyzed (E)-Selective Isomerization of Alkenes

B. A. Kustiana, S. A. Elsherbeni, T. G. Linford-Wood, R. L. Melen, M. N. Grayson and L. C. Morrill*, Chem. Eur. J., 2022, 28, e202202454.

(53)

Electrochemical Alkene Azidocyanation via 1,4-Nitrile Migration

A. C. Seastram, M. D. Hareram, T. M. B. Knight and L. C. Morrill*, Chem. Commun., 2022, 58, 8658-8662.

(52)

Electrochemical Deconstructive Functionalization of Cycloalkanols via Alkoxy Radicals Enabled by Proton-Coupled Electron Transfer

M. Deepak Hareram, A. A. M. A. El Gehani, J. Harnedy, A. C. Seastram, A. C. Jones, M. Burns, T. Wirth, D. L. Browne and L. C. Morrill*, Org. Lett., 2022, 24, 3890-3895.

(51)

Mechanochemical Organocatalysis: Do High Enantioselectivities Contradict what we Might Expect?

M. T. J. Williams, L. C. Morrill* and D. L. Browne*, ChemSusChem, 2022, 15, e202102157.

(50)

The Role of Streptavidin and its Variants in Catalysis by Biotinylated Secondary Amines

A. R. Nödling, N. Santi, R. Castillo, M. Lipka-Lloyd, Y. Jin, L. C. Morrill, K. Swiderek*, V. Moliner* and L. Y. P. Luk*, Org. Biomol. Chem., 2021, 19, 10424-10431.

(49)

J. Harnedy, M. D. Hareram, G. J. Tizzard, S. J. Coles and L. C. Morrill*, Chem. Commun., 2021, 57, 12643-12646. [Invited contribution to the 2021 Emerging Investigators themed collection]

Electrochemical oxidative Z-selective C(sp2)-H chlorination of acrylamides

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W. I. Nicholson, J. L. Howard, G. Magri, A. C. Seastram, A. Khan, R. R. A. Bolt, L. C. Morrill, E. Richards and D. L. Browne*, Angew. Chem. Int. Ed., 2021, 60, 23128-23133.

Ball Milling Enabled Reactivity of Manganese Metal

(47)

Borrowing Hydrogen for Organic Synthesis

B. G. Reed-Berendt,† D. E. Latham,† M. B. Dambatta and L. C. Morrill*, ACS Cent. Sci., 2021, 7, 570-585.

(46)

Electron deficient borane-mediated hydride abstraction in amines: stoichiometric and catalytic processes

S. Basak, L. Winfrey, B. A. Kustiana, R. L. Melen*, L. C. Morrill* and A. P. Pulis*, Chem. Soc. Rev., 2021, 50, 3720-3737.

(45)

Transfer Hydrogenations Catalyzed by Steptavidin-hosted Secondary Amine Organocatalyst

N. Santi, L. C. Morrill, K. Swiderek, V. Moliner and L. Y. P. Luk*, Chem. Commun., 2021, 57, 1919-1922.

(44)

Expedient Organocatalytic Aza-Morita-Baylis-Hillman Reaction Through Ball-Milling

M. T. J. Williams, L. C. Morrill* and D. L. Browne*, ACS Sustainable Chem. Eng., 2020, 8, 17876-17881.

(43)

Transition Metal Free α-C-Alkylation of Ketones Using Secondary Alcohols

M. B. Dambatta, J. Santos, R. R. A. Bolt and L. C. Morrill*, Tetrahedron, 2020, 76, 131571. [Invited contribution to the Special Issue on Strategies for Efficient Organic Synthesis Dedicated to the Achievements of Prof. Jonathan Williams]

(42)

Streptavidin-hosted Organocatalytic Aldol Addition

N. Santi, L. C. Morrill and L. Y. P. Luk*, Molecules, 2020, 25, 2457. [Invited contribution to the Hybrid Catalysts for Asymmetric Catalysis Special Issue]

(41)

B(C6F5)3-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles

S. Basak, A. Alvarez-Montoya, L. Winfrey, R. L. Melen*, L. C. Morrill* and A. P. Pulis*, ACS Catal., 2020, 10, 4835-4840.

(40)

Manganese-Catalyzed One-Pot Conversion of Nitroarenes into N-Methylarylamines Using Methanol

B. G. Reed-Berendt, N. Mast and L. C. Morrill*, Eur. J. Org. Chem., 2020, 1136-1140. [Invited contribution to the YourJOC Talents Special Issue]

(39)

N-Heterocyclic Carbene Acyl Anion Organocatalysis by Ball-Milling

W. I. Nicholson, A. C. Seastram, S. A. Iqbal, B. G. Reed-Berendt, L. C. Morrill* and D. L. Browne*, ChemSusChem, 2020, 13, 131-135. [Hot Topic: Organocatalysis]

(38)

Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals

B. D. W. Allen,† M. D. Hareram,† A. C. Seastram, T. McBride, T. Wirth, D. L. Browne* and L. C. Morrill*, Org. Lett., 2019, 21, 9241-9246. [Associated correction to citations]

(37)

One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization-Methylation

D. E. Latham, K. Polidano, J. M. J. Williams and L. C. Morrill*, Org. Lett., 2019, 21, 7914-7918.

(36)

Iron-Catalyzed Borrowing Hydrogen β-C(sp3)-Methylation of Alcohols

K. Polidano, J. M. J. Williams and L. C. Morrill*, ACS Catal., 2019, 9, 8575-8580. [Highlighted in Synfacts, 2019, 15, 1280]

(35)

Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles Using Alcohols

M. B. Dambatta, K. Polidano, A. D. Northey, J. M. J. Williams and L. C. Morrill*, ChemSusChem, 2019, 12, 2345-2349.

(34)

Manganese-Catalyzed N-Alkylation of Sulfonamides Using Alcohols

B. G. Reed-Berendt and L. C. Morrill*, J. Org. Chem., 2019, 84, 3715-3724. [Highlighted in Organic Chemistry Portal]

(33)

Recent Advances in Homogeneous Borrowing Hydrogen Catalysis using Earth-Abundant First Row Transition Metals

B. G. Reed-Berendt, K. Polidano and L. C. Morrill*, Org. Biomol. Chem., 2019, 17, 1595-1607. [Invited contribution to the New Talent Special Issue]

(32)

FLP-Catalyzed Transfer Hydrogenation of Silyl Enol Ethers

I. Khan, B. G. Reed-Berendt, R. L. Melen* and L. C. Morrill*, Angew. Chem. Int. Ed., 2018, 57, 12356-12359.

(31)

Synthesis and Reactivity of N-Allenyl Cyanamides

J. N. Ayres, M. T. J. Williams, G. J. Tizzard, S. J. Coles, K. B. Ling and L. C. Morrill*, Org. Lett., 2018, 20, 5282-5285.

(30)

Reactivity and Selectivity of Iminium Organocatalysis Improved by a Protein Host

A. R. Nödling, K. Swiderek, R. Castillo, J. W. Hall, A. Angelastro, L. C. Morrill, Y. Jin, Y-H. Tsai, V. Moliner* and L. Y. P. Luk*, Angew. Chem. Int. Ed., 2018, 57, 12478-12482.

(29)

Iron-Catalyzed Methylation using the Borrowing Hydrogen Approach

K. Polidano, B. D. W. Allen, J. M. J. Williams and L. C. Morrill*, ACS Catal., 2018, 8, 6440-6445.

(28)

Exploring Tandem Ruthenium-Catalyzed Hydrogen Transfer and SNAr Chemistry

K. Polidano, B. G. Reed-Berendt, A. Basset, A. J. A. Watson, J. M. J. Williams and L. C. Morrill*, Org. Lett., 2017, 19, 6716-6719.

(27)

Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Aza-Morita-Baylis-Hillman Adducts and Sequential Organo-FLP Catalysis

I. Khan, M. Manzotti, G. J. Tizzard, S. J. Coles, R. L. Melen* and L. C. Morrill*, ACS Catal., 2017, 7, 7748-7752.

(26)

Deoxycyanamidation of Alcohols with N-Cyano-N-Phenyl-p-Methylbenzenesulfonamide (NCTS)

J. N. Ayres, M. W. Ashford, Y. Stöckl, V. Prudhomme, K. B. Ling, J. A. Platts and L. C. Morrill*, Org. Lett., 2017, 19, 3835-3838.

(25)

N-Cyanation of Secondary Amines using Trichloroacetonitrile

J. N. Ayres, K. B. Ling* and L. C. Morrill*, Org. Lett., 2016, 18, 5528-5531.

Postdoctoral Publications (UC Berkeley with Prof. Richmond Sarpong):

(24)

A Benzyne-Insertion Approach to Hetisine-Type Diterpenoid Alkaloids: Synthesis of Cossonidine (Davisine)

K. G. M. Kou, J. J. Pflueger, T. Kiho, L. C. Morrill, E. L. Fisher, K. Clagg, T. P. Lebold, J. K. Kisunzu* and R. Sarpong*, J. Am. Chem. Soc., 2018, 140, 8105-8109.

(23)

A Magnesiate Addition/Ring-Expansion Strategy to Access the 6-7-6 Tricyclic Core of Hetisine-type C20-Diterpenoid Alkaloids

J. J. Pflueger, L. C. Morrill, J. N. deGruyter, M. A. Perea and R. Sarpong*, Org. Lett., 2017, 19, 4632-4635.

(22)

Palladium-catalyzed β-Selective C(sp3)-H Arylation of N-Boc-Piperidines

A. Millet and O. Baudoin*; checked by L. C. Morrill and R. Sarpong, Org. Synth., 2015, 92, 76-90.

Postgraduate Publications (University of St Andrews with Prof. Andrew D. Smith):

(21)

Catalytic Generation of Ammonium Enolates and Related Tertiary Amine-Derived Intermediates: Applications, Mechanism and Stereochemical Models (n→π*)

K. N. Van, L. C. Morrill, A. D. Smith and D. Romo, Book Chapter within “Lewis Base Catalysis in Organic Synthesis”, ed. E. Vedejs and S. E. Denmark, Wiley, Weinheim, 2016.

(20)

Enantioselective Synthesis of 3,5,6-Substituted Dihydropyranones and Dihydropyridinones using Isothiourea-Mediated Catalysis

D. B. Cordes, A. M. Z. Slawin, T. J. C. O’Riordan and A. D. Smith*, Chem. Asian J., 2016, 11, 395-400. [Special Issue: Catalysis and Transformation of Complex Molecules]

(19)

Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines

S. R. Smith, C. Fallan, J. E. Taylor, R. McLennan, D. S. B. Daniels, L. C. Morrill, A. M. Z. Slawin and A. D. Smith*, Chem. Eur. J., 2015, 21, 10530-10536.

(18)

Organocatalytic Michael Addition-Lactonisation of Carboxylic Acids using α,β-Unsaturated Trichloromethyl Ketones as α,β-Unsaturated Ester Equivalents

L. C. Morrill, D. G. Stark, J. E. Taylor, S. R. Smith, J. A. Squires, A. C. A. D’Hollander, C. Simal, P. Shapland, T. J. C. O’Riordan and A. D. Smith*, Org. Biomol. Chem., 2014, 12, 9016-9027. [Highlighted in Synfacts, 2015, 11, 315] [Part of themed collection: 2014 Hot Articles in Organic and Biological Chemistry]

(17)

Organocatalytic Lewis base functionalisation of carboxylic acids and esters via ammonium/azolium enolates

L. C. Morrill and A. D. Smith*, Chem. Soc. Rev., 2014, 43, 6214-6226. [One of the most accessed articles in Chem. Soc. Rev. during June 2014]

(16)

Lewis Base Catalysed Asymmetric [2+2] Cycloadditions

A. D. Smith, J. Douglas, L. C. Morrill and E. Richmond, Book Chapter within “Methods and Applications of Cycloaddition Reactions in Organic Synthesis” , ed. N. Nishiwaki, Wiley, New York, 2014.

(15)

Isothiourea-Mediated Asymmetric Functionalization of 3-Alkenoic Acids

L. C. Morrill, S. M. Smith, A. M. Z. Slawin and A. D. Smith*, J. Org. Chem., 2014, 79, 1640-1655.

(14)

2-Arylacetic anhydrides as ammonium enolate precursors

L. C. Morrill, L. A. Ledingham, J-P. Couturier, J. Bickel, A. Harper, C. Fallan and A. D. Smith*, Org. Biomol. Chem., 2014, 12, 624-636.

(13)

Isothiourea-Mediated One-Pot Synthesis of Functionalized Pyridines

D. G. Stark, L. C. Morrill, P-P. Yeh, A. M. Z. Slawin, T. J. C. O’Riordan and A. D. Smith*, Angew. Chem. Int. Ed., 2013, 52, 11642-11646. [Selected as a Hot Paper] [Highlighted in Synfacts, 2013, 9, 1344] [Highlighted in Org. Chem. Highlights, 2014, June 23]

(12)

Stereospecific Asymmetric N-Heterocyclic Carbene (NHC)-Catalyzed Redox Synthesis of Trifluoromethyl Dihydropyranones and Mechanistic Insights

A. T. Davies, J. E. Taylor, J. Douglas, C. J. Collett, L. C. Morrill, C. Fallan, A. M. Z. Slawin and A. D. Smith*, J. Org. Chem., 2013, 78, 9243-9257.

(11)

Isothiourea-mediated asymmetric Michael-lactonisation of trifluoromethylenones: a synthetic and mechanistic study

L. C. Morrill, J. Douglas, T. Lebl, D. J. Fox, A. M. Z. Slawin and A. D. Smith*, Chem. Sci., 2013, 4, 4146-4155. [One of the most accessed articles in Chem. Sci. during August 2013] [Part of themed collection: Celebrating the 2014 RSC Prize and Award Winners]

(10)

Catalytic asymmetric α-amination of carboxylic acids using isothioureas

L. C. Morrill, T. Lebl, A. M. Z. Slawin and A. D. Smith*, Chem. Sci., 2012, 3, 2088-2093.

(9)

Organocatalytic Functionalisation of Carboxylic Acids: Isothiourea-Catalysed Asymmetric Intra- and Intermolecular Michael Addition-Lactonisations

D. Belmessieri, L. C. Morrill, C. Simal, A. M. Z. Slawin and A. D. Smith*, J. Am. Chem. Soc., 2011, 133, 2714-2720. [Highlighted in Synfacts, 2011, 4, 436]

Undergraduate Publications (University of St Andrews):

(8)

Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates

C. D. Campbell, C. Joannesse, L. C. Morrill, D. Philp and A. D. Smith*, Org. Biomol. Chem., 2015, 13, 2895-2900. [Part of themed collection: 2015 Hot Articles in Organic and Biomolecular Chemistry]

(7)

Efficacious, inhaled PDE4 inhibitors with low emetic potential and long duration of action, for the treatment of COPD

C. De Savi*, R. J. Cox*, D. Warner, A. R. Cook, M. R. Dickinson, A. McDonough, L. C. Morrill, B. Parker, G. Andrews, S. Young, P. S. Gilmour, R. Riley and M. S. Dearman, J. Med. Chem., 2014, 57, 4661-4676.

(6)

Isothiourea-Mediated Asymmetric O- to C-Carboxyl Transfer of Oxazoyl Carbonates: Structure-Selectivity Profiles and Mechanistic Studies

C. Joannesse, C. P. Johnston, L. C. Morrill, P. A. Woods, M. Kieffer, T. A. Nigst, H. Mayr, T. Lebl, D. Philp, R. A. Bragg and A. D. Smith*, Chem. Eur. J., 2012, 18, 2398-2408.

(5)

Isothiourea-Catalyzed Asymmetric C-Acylation of Silyl Ketene Acetals

P. A. Woods, L. C. Morrill, R. A. Bragg and A. D. Smith*, Chem. Eur. J., 2011, 17, 11060-11067.

(4)

Isothiourea-catalyzed asymmetric O- to C-carboxyl transfer of furanyl carbonates

C. Joannesse, L. C. Morrill, C. D. Campbell, A. M. Z. Slawin and A. D. Smith*, Synthesis, 2011, 1865-1879.

(3)

Isothiourea-Mediated Stereoselective C-acylation of Silyl Ketene Acetals

P. A. Woods, L. C. Morrill, T Lebl, A. M. Z. Slawin, R. A. Bragg and A. D. Smith*, Org. Lett., 2010, 12, 2660-2663

(2)

Unexpected Rearrangement Leading to Formation of a 1,3-Bis(triphenylphosponio)prop-1-en-3-idyl Carboxylate

R. A. Aitken*, L. P. Cleghorn, R. M. Leitch, L. C. Morrill and A. M. Z. Slawin, Eur. J. Org. Chem., 2010, 3211-3214.

(1)

N-heterocyclic carbene catalysed O- to C-carboxyl transfer of indolyl and benzofuranyl carbonates

J. E. Thomson, A. F. Kyle, C. Concellón, K. A. Gallagher, P. Lenden, L. C. Morrill, A. J. Miller, C. Joannesse, A. M. Z. Slawin and A. D. Smith*, Synthesis, 2008, 2805-2818.