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HON LAM's Outputs (32)

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, 15(36), 14685-14691. 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.

Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines (2016)
Journal Article
Smith, J. J., Best, D., & Lam, H. W. (2016). Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines. Chemical Communications, https://doi.org/10.1039/C6CC00603E

Cu-catalyzed three-component couplings of vinylazaarenes, B2(pin)2, and N-Boc imines are described. Oxidation of the initially formed boronate gives azaarene-containing, Boc-protected amino alcohols with reasonable to good diastereoselectivities.

Chain walking of allylrhodium species towards esters during rhodium-catalyzed nucleophilic allylations of imines (2015)
Journal Article
Martínez, J. I., Smith, J. S., Hepburn, H. B., & Lam, H. W. (2016). Chain walking of allylrhodium species towards esters during rhodium-catalyzed nucleophilic allylations of imines. Angewandte Chemie International Edition, 55(3), 1108-1112. https://doi.org/10.1002/anie.201508964

Allylrhodium species derived from δ-trifluoroboryl β,γ-unsaturated esters undergo chain walking towards the ester moiety.The resulting allylrhodium species react with imines to give products containing two new stereocenters and a Z-alkene. By using a... Read More about Chain walking of allylrhodium species towards esters during rhodium-catalyzed nucleophilic allylations of imines.

Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C—H Functionalization and Spiroannulation (2015)
Journal Article
Reddy Chidipudi, S., Burns, D. J., Khan, I., & Lam, H. W. (2015). Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C—H Functionalization and Spiroannulation. Angewandte Chemie International Edition, 54(47), 13975-13979. https://doi.org/10.1002/anie.201507029

Chiral cyclopentadienyl rhodium complexes promote highly enantioselective enol‐directed C(sp2)‐H functionalization and oxidative annulation with alkynes to give spiroindenes containing all‐carbon quaternary stereocenters. High selectivity between two... Read More about Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C—H Functionalization and Spiroannulation.

Direct Synthesis of 5-Aryl Barbituric Acids by Rhodium(II)-Catalyzed Reactions of Arenes with Diazo Compounds (2015)
Journal Article
Best, D., Burns, D. J., & Lam, H. W. (2015). Direct Synthesis of 5-Aryl Barbituric Acids by Rhodium(II)-Catalyzed Reactions of Arenes with Diazo Compounds. Angewandte Chemie International Edition, 54(25), 7410-7413. https://doi.org/10.1002/anie.201502324

A commercially available rhodium(II) complex catalyzes the direct arylation of 5‐diazobarbituric acids with arenes, allowing straightforward access to 5‐aryl barbituric acids. Free N--H groups are tolerated on the barbituric acid, with no complicatio... Read More about Direct Synthesis of 5-Aryl Barbituric Acids by Rhodium(II)-Catalyzed Reactions of Arenes with Diazo Compounds.

Enantioselective copper-catalyzed reductive coupling of vinylazaarenes with N-Boc aldimines (2015)
Journal Article
Choi, B., Saxena, A., Smith, J. J., Churchill, G. H., & Lam, H. W. (2015). Enantioselective copper-catalyzed reductive coupling of vinylazaarenes with N-Boc aldimines. SYNLETT, 26(3), https://doi.org/10.1055/s-0034-1379548

The diastereo- and enantioselective reductive coupling of vinylazaarenes with N-Boc aldimines is described. The reactions proceed using chiral copper–bisphosphine complexes in the presence of TMDS as a hydride source to give reductive coupling produc... Read More about Enantioselective copper-catalyzed reductive coupling of vinylazaarenes with N-Boc aldimines.

Synthesis of spiroindanes by palladium-catalyzed oxidative annulations of non- or weakly activated 1,3-dienes involving C–H functionalization (2015)
Journal Article
Khan, I., Chidipudi, S. R., & Lam, H. W. (2015). Synthesis of spiroindanes by palladium-catalyzed oxidative annulations of non- or weakly activated 1,3-dienes involving C–H functionalization. Chemical Communications, 51, https://doi.org/10.1039/C4CC09496D

The synthesis of spiroindanes by the palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes with 2-aryl cyclic 1,3-dicarbonyl compounds is described. Examples of the dearomatizing oxidative annulation of 1,3-dienes with 1-ary... Read More about Synthesis of spiroindanes by palladium-catalyzed oxidative annulations of non- or weakly activated 1,3-dienes involving C–H functionalization.

Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations (2014)
Journal Article

1,3?Enynes containing allylic hydrogens cis to the alkyne are shown to act as one?carbon partners, rather than two?carbon partners, in various rhodium?catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to o... Read More about Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations.

Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes (2014)
Journal Article
Kujawa, S., Best, D., Burns, D. J., & Lam, H. W. (2014). Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes. Chemistry - A European Journal, 20(28), https://doi.org/10.1002/chem.201403454

The dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes proceeds with high yields and regioselectivities under Rh(III) catalysis. These reactions are successful using Cu(OAc)2 or air as the stoichiometric oxidant, and provi... Read More about Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes.

Enantioselective synthesis of allylboronates and allylic alcohols by copper-catalyzed 1,6-boration (2014)
Journal Article
Luo, Y., Roy, I. D., Madec, A. G., & Lam, H. W. (2014). Enantioselective synthesis of allylboronates and allylic alcohols by copper-catalyzed 1,6-boration. Angewandte Chemie International Edition, 53(16), https://doi.org/10.1002/anie.201310380

Chiral secondary allylboronates are obtained in high enantioselectivities by the copper-catalyzed 1,6-boration of electron-deficient dienes with B2(pin)2. The reactions proceed efficiently using catalyst loadings as low as 0.0049 mol%. The allylboron... Read More about Enantioselective synthesis of allylboronates and allylic alcohols by copper-catalyzed 1,6-boration.

A second-generation ligand for the enantioselective rhodium-catalyzed addition of arylboronic acids to alkenylazaarenes (2014)
Journal Article
Roy, I. D., Burns, A. R., Pattison, G., Michel, B., Parker, A. J., & Lam, H. W. (2014). A second-generation ligand for the enantioselective rhodium-catalyzed addition of arylboronic acids to alkenylazaarenes. Chemical Communications, 50(22), https://doi.org/10.1039/C4CC00340C

A 2,4,6-trialkylanilide-containing chiral diene has been identified as a superior ligand for the enantioselective rhodiumcatalyzed arylation of alkenylazaarenes with arylboronic acids.

C=N-containing azaarenes as activating groups in enantioselective catalysis (2013)
Journal Article
Best, D., & Lam, H. W. (2013). C=N-containing azaarenes as activating groups in enantioselective catalysis. Journal of Organic Chemistry, 79(3), https://doi.org/10.1021/jo402414k

Nitrogen-containing aromatic heterocycles (azaarenes) are of widespread chemical significance, and chi-ral compounds containing azaarenes feature prominently in pharmaceuticals, agrochemicals, and natural products. This Perspective highlights the use... Read More about C=N-containing azaarenes as activating groups in enantioselective catalysis.