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Organofunctionalized borotungstate polyoxometalates as tunable photocatalysts for oxidative dimerization of amines (2024)
Journal Article
Tsang, N., Kibler, A. J., Argent, S. P., Lam, H. W., Jones, K. D., & Newton, G. N. (2024). Organofunctionalized borotungstate polyoxometalates as tunable photocatalysts for oxidative dimerization of amines. Chemical Science, https://doi.org/10.1039/d4sc03534h

Organofunctionalized borotungstate Keggin polyoxometalates, (nBu4N)3H[HBW11O39(P(O)Ph)2] (PBW11), (nBu4N)3H[HBW11O39(As(O)Ph)2] (AsBW11), and (nBu4N)4[HBW11O39(PhSiOSiPh)] (SiBW11), were synthesized and structurally characterized. Cyclic voltammetry... Read More about Organofunctionalized borotungstate polyoxometalates as tunable photocatalysts for oxidative dimerization of amines.

Nickel‐Catalysed syn‐Selective Arylnickelation and Cyclisation of Ketone/Imine‐Tethered Terminal Alkynes with Arylboronic Acids (2024)
Journal Article
Morgan, D. M., Lam, H. W., & Guiry, P. J. (2024). Nickel‐Catalysed syn‐Selective Arylnickelation and Cyclisation of Ketone/Imine‐Tethered Terminal Alkynes with Arylboronic Acids. European Journal of Organic Chemistry, 27(23), Article e202400445. https://doi.org/10.1002/ejoc.202400445

Herein we report a syn-arylnickelative cyclisation with ketone- and imine-tethered terminal alkynes (16 examples) in yields of up to 89 %. The reaction proceeds via a syn-aryl nickelation of a terminal alkyne followed by cyclisation of the resulting... Read More about Nickel‐Catalysed syn‐Selective Arylnickelation and Cyclisation of Ketone/Imine‐Tethered Terminal Alkynes with Arylboronic Acids.

Enantioselective de novo synthesis of 14-hydroxy-6-oxomorphinans (2024)
Journal Article
Moore, J. C., Modell, L., Glenn, J. R., Jones, K. D., Argent, S. P., Lane, J. R., …Lam, H. W. (2024). Enantioselective de novo synthesis of 14-hydroxy-6-oxomorphinans. Chemical Communications, 60(47), 6007-6010. https://doi.org/10.1039/d4cc01788a

The enantioselective de novo synthesis of pharmacologically important 14-hydroxy-6-oxomorphinans is described. 4,5-Desoxynaltrexone and 4,5-desoxynaloxone were prepared using this route and their biological activities against the opioid receptors wer... Read More about Enantioselective de novo synthesis of 14-hydroxy-6-oxomorphinans.

Silver(I)-Catalyzed Synthesis of Cuneanes from Cubanes and their Investigation as Isosteres (2023)
Journal Article
Smith, E., Jones, K. D., O’Brien, L., Argent, S. P., Salome, C., Lefebvre, Q., …Lam, H. W. (2023). Silver(I)-Catalyzed Synthesis of Cuneanes from Cubanes and their Investigation as Isosteres. Journal of the American Chemical Society, 145(30), 16365-16373. https://doi.org/10.1021/jacs.3c03207

Bridged or caged polycyclic hydrocarbons have rigid structures that project substituents into precise regions of 3D space, making them attractive as linking groups in materials science and as building blocks for medicinal chemistry. The efficient syn... Read More about Silver(I)-Catalyzed Synthesis of Cuneanes from Cubanes and their Investigation as Isosteres.

Diphosphoryl‐functionalized Polyoxometalates: Structurally and Electronically Tunable Hybrid Molecular Materials (2023)
Journal Article
Amin, S. S., Jones, K. D., Kibler, A. J., Damian, H. A., Cameron, J. M., Butler, K. S., Argent, S. P., Winslow, M., Robinson, D., Mitchell, N. J., Lam, H. W., & Newton, G. N. (2023). Diphosphoryl‐functionalized Polyoxometalates: Structurally and Electronically Tunable Hybrid Molecular Materials. Angewandte Chemie International Edition, 62(23), Article e202302446. https://doi.org/10.1002/anie.202302446

Herein, we report the synthesis and characterization of a new class of hybrid Wells–Dawson polyoxometalate (POM) containing a diphosphoryl group (P2O6X) of the general formula [P2W17O57(P2O6X)]6− (X=O, NH, or CR1R2). Modifying the bridging unit X was... Read More about Diphosphoryl‐functionalized Polyoxometalates: Structurally and Electronically Tunable Hybrid Molecular Materials.

Electronic Structure and Photoactivity of Organoarsenic Hybrid Polyoxometalates (2023)
Journal Article
Kibler, A. J., Tsang, N., Winslow, M., Argent, S. P., Lam, H. W., Robinson, D., & Newton, G. N. (2023). Electronic Structure and Photoactivity of Organoarsenic Hybrid Polyoxometalates. Inorganic Chemistry, 62(8), 3585-3591. https://doi.org/10.1021/acs.inorgchem.2c04249

Organofunctionalization of polyoxometalates (POMs) allows the preparation of hybrid molecular systems with tunable electronic properties. Currently, there are only a handful of approaches that allow for the fine-tuning of POM frontier molecular orbit... Read More about Electronic Structure and Photoactivity of Organoarsenic Hybrid Polyoxometalates.

A Scalable Synthesis of Chiral Himbert Diene Ligands for Asymmetric Catalysis (2023)
Journal Article
Rit, R., Li, H., Argent, S. P., Wheelhouse, K. M., Woodward, S., & Lam, H. W. (2023). A Scalable Synthesis of Chiral Himbert Diene Ligands for Asymmetric Catalysis. Advanced Synthesis and Catalysis, 365(10), 1629-1639. https://doi.org/10.1002/adsc.202300039

Chiral dienes are important ligands in asymmetric catalysis but they are less accessible than other commonly used ligands such as chiral bisphosphines. Here, we show that intramolecular [4 + 2] cycloaddition of a simply attained chiral allenecarboxan... Read More about A Scalable Synthesis of Chiral Himbert Diene Ligands for Asymmetric Catalysis.

Synthesis of New Morphinan Opioids by TBADT‐Catalyzed Photochemical Functionalization at the Carbon Skeleton (2022)
Journal Article
Gorbachev, D., Smith, E., Argent, S. P., Newton, G. N., & Lam, H. W. (2022). Synthesis of New Morphinan Opioids by TBADT‐Catalyzed Photochemical Functionalization at the Carbon Skeleton. Chemistry - A European Journal, 28(50), Article e202201478. https://doi.org/10.1002/chem.202201478

The synthesis of new morphinan opioids by the addition of photochemically generated carbon-centered radicals to substrates containing an enone in the morphinan C-ring, is described. Using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom tr... Read More about Synthesis of New Morphinan Opioids by TBADT‐Catalyzed Photochemical Functionalization at the Carbon Skeleton.

Frontispiece: Nickel‐Catalyzed Arylative Cyclizations of Alkyne‐ and Allene‐Tethered Electrophiles using Arylboron Reagents (2022)
Journal Article
Gillbard, S. M., & Lam, H. W. (2022). Frontispiece: Nickel‐Catalyzed Arylative Cyclizations of Alkyne‐ and Allene‐Tethered Electrophiles using Arylboron Reagents. Chemistry - A European Journal, 28(18), Article e202281862. https://doi.org/10.1002/chem.202281862

This review summarizes recent progress in nickel-catalyzed arylative cyclizations of alkyne- and allene-tethered electrophiles using arylboron reagents, which are useful methods for the preparation of diverse carbo- and heterocyclic products. In many... Read More about Frontispiece: Nickel‐Catalyzed Arylative Cyclizations of Alkyne‐ and Allene‐Tethered Electrophiles using Arylboron Reagents.

Gold(I)-Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates (2022)
Journal Article
O'Brien, L., Argent, S. P., Ermanis, K., & Lam, H. W. (2022). Gold(I)-Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates. Angewandte Chemie International Edition, 61(22), Article e202202305. https://doi.org/10.1002/anie.202202305

Gold(I)-catalyzed nucleophilic allylations of pyridinium and quinolinium ions with allylboronates are reported. Transmetalation of the allylboronate with gold produces nucleophilic allylgold(I) species that add to the 4-position of the azinium ion wi... Read More about Gold(I)-Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates.

Nickel‐Catalyzed Arylative Cyclizations of Alkyne‐ and Allene‐Tethered Electrophiles using Arylboron Reagents (2022)
Journal Article
Gillbard, S. M., & Lam, H. W. (2022). Nickel‐Catalyzed Arylative Cyclizations of Alkyne‐ and Allene‐Tethered Electrophiles using Arylboron Reagents. Chemistry - A European Journal, 28(18), Article e202104230. https://doi.org/10.1002/chem.202104230

The use of arylboron reagents in metal-catalyzed domino addition–cyclization reactions is a well-established strategy for the preparation of diverse, highly functionalized carbo- and heterocyclic products. Although rhodium- and palladium-based cataly... Read More about Nickel‐Catalyzed Arylative Cyclizations of Alkyne‐ and Allene‐Tethered Electrophiles using Arylboron Reagents.

Enantioselective nickel-catalyzed anti-arylmetallative cyclizations onto acyclic electron-deficient alkenes (2021)
Journal Article
Gillbard, S. M., Green, H., Argent, S. P., & Lam, H. W. (2021). Enantioselective nickel-catalyzed anti-arylmetallative cyclizations onto acyclic electron-deficient alkenes. Chemical Communications, 57(36), 4436-4439. https://doi.org/10.1039/d1cc01166a

Enantioselective nickel-catalyzed reactions of (hetero)arylboronic acids or alkenylboronic acids with substrates containing an alkyne tethered to various acyclic electron-deficient alkenes are described.

Enantioselective Nickel‐Catalyzed anti ‐Arylmetallative Cyclizations onto Acyclic Ketones (2021)
Journal Article
Green, H., Argent, S., & Lam, H. (2021). Enantioselective Nickel‐Catalyzed anti ‐Arylmetallative Cyclizations onto Acyclic Ketones. Chemistry - A European Journal, 27(19), 5897-5900. https://doi.org/10.1002/chem.202100143

Domino reactions involving nickel‐catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization of the alkenylnickel intermediates onto tethered acyclic ketones to give chiral tertiary‐alcohol‐containing products in high enanti... Read More about Enantioselective Nickel‐Catalyzed anti ‐Arylmetallative Cyclizations onto Acyclic Ketones.

Remote Nucleophilic Allylation by Allylrhodium Chain Walking (2018)
Journal Article
Martínez, J. I., Groves, A., Martinez, J. I., Smith, J. J., & Lam, H. W. (2018). Remote Nucleophilic Allylation by Allylrhodium Chain Walking. Chemistry - A European Journal, 24(51), 13432-13436. https://doi.org/10.1002/chem.201803574

Metal migration through a carbon chain is a versatile method for achieving remote functionalization. However, almost all known examples involve the overall net migration of alkylmetal species. Here, we report that allylrhodium species obtained from h... Read More about Remote Nucleophilic Allylation by Allylrhodium Chain Walking.

Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters (2018)
Journal Article
Karad, S. N., Panchal, H., Clarke, C., Lewis, W., & Lam, H. W. (2018). Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters. Angewandte Chemie International Edition, 57(29), 9122-9125. https://doi.org/10.1002/anie.201805578

The enantioselective synthesis of highly functionalized chiral cyclopent‐2‐enones by the reaction of alkynyl malonate esters with arylboronic acids is described. These desymmetrizing arylative cyclizations are catalyzed by a chiral phosphinooxazoline... Read More about Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters.

Enantioselective nickel-catalyzed arylative intramolecular 1,4allylations (2018)
Journal Article
Nguyen, T. L. N., Incerti-Pradillos, C. A., Lewis, W., & Lam, H. W. (in press). Enantioselective nickel-catalyzed arylative intramolecular 1,4allylations. Chemical Communications, https://doi.org/10.1039/C8CC03204A

The enantioselective nickel-catalyzed desymmetrization of allenyl cyclohexa-2,5-dienones by reaction with arylboronic acids is described. Nickel-catalyzed arylation of the allene gives allylnickel species, which undergo cyclization by 1,4allylation t... Read More about Enantioselective nickel-catalyzed arylative intramolecular 1,4allylations.

Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration (2018)
Journal Article
Luo, Y., Wales, S. M., Korkis, S. E., Roy, I. D., Lewis, W., & Lam, H. W. (2018). Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration. Chemistry - A European Journal, 24(33), 8315-8319. https://doi.org/10.1002/chem.201801804

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The enantioselective Cu-catalyzed 1,6-boration of (E,E)-α,β,γ,δ-unsaturated ketones is described, which gives homoallylic boronates with high enantiomeric purity and unexpectedly high Z-selectivity.... Read More about Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration.

One-carbon oxidative annulations of 1,3-enynes by catalytic C–H functionalization and 1,4-rhodium(III) migration (2018)
Journal Article
Dooley, J. D., & Lam, H. W. (2018). One-carbon oxidative annulations of 1,3-enynes by catalytic C–H functionalization and 1,4-rhodium(III) migration. Chemistry - A European Journal, 24(16), 4050-4054. https://doi.org/10.1002/chem.201706043

Rhodium(III)-catalyzed C-H functionalization-oxidative annulations of aromatic substrates with 1,3-enynes that contain allylic hydrogen atoms cis to the alkyne are described. The key step in these reactions is an alkenyl-to-allyl 1,4-rhodium(III) mig... Read More about One-carbon oxidative annulations of 1,3-enynes by catalytic C–H functionalization and 1,4-rhodium(III) migration.

Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration (2016)
Journal Article
Korkis, S. E., Burns, D. J., & Lam, H. W. (in press). Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration. Journal of the American Chemical Society, https://doi.org/10.1021/jacs.6b06884

The Rh(III)-catalyzed oxidative C–H allylation of N-acetylbenzamides with 1,3-dienes is described. The presence of allylic hydrogens cis- to the less substituted alkene of the 1,3-diene is important for the success of these reactions. With the assist... Read More about Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration.