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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.

Hydroperoxide-Mediated Degradation of Acetonitrile in the Lithium–Air Battery (2023)
Journal Article
McNulty, R. C., Jones, K. D., Holc, C., Jordan, J. W., Bruce, P. G., Walsh, D. A., …Johnson, L. R. (2023). Hydroperoxide-Mediated Degradation of Acetonitrile in the Lithium–Air Battery. Advanced Energy Materials, 13(3), Article 2300579. https://doi.org/10.1002/aenm.202300579

Understanding and eliminating degradation of the electrolyte solution is arguably the major challenge in the development of high energy density lithium–air batteries. The use of acetonitrile provides cycle stability comparable to current state-of-the... Read More about Hydroperoxide-Mediated Degradation of Acetonitrile in the Lithium–Air Battery.

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., …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.

Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration (2020)
Journal Article
Groves, A., Sun, J., Parke, H. R. I., Callingham, M., Argent, S. P., Taylor, L. J., & Lam, H. W. (2020). Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration. Chemical Science, 11(10), 2759–2764. https://doi.org/10.1039/c9sc06309a

The enantioselective synthesis of densely functionalized polycarbocycles by the rhodium(I)-catalyzed reaction of arylboronic acids with 1,3-diketones is described. The key step in these desymmetrizing domino addition–cyclization reactions is an alken... Read More about Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration.

Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(I) migration (2019)
Journal Article
O'Brien, L., Karad, S. N., Lewis, W., & Lam, H. W. (2019). Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(I) migration. Chemical Communications, 55(76), 11366-11369. https://doi.org/10.1039/c9cc05205d

The synthesis of functionalized 1-tetralones by the rhodium(I)-catalyzed reaction of alkynyl malonates with arylboronic acids is described. These arylative cyclizations proceed via an alkenyl-to-aryl 1,4-Rh(I) migration as a key step. Preliminary res... Read More about Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(I) migration.

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 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.

Enantioselective rhodium-catalyzed coupling of arylboronic acids, 1,3-enynes, and Imines by alkenyl-to-allyl 1,4-rhodium(I) migration (2017)
Journal Article
Callingham, M., Partridge, B. M., Lewis, W., & Lam, H. W. (2017). Enantioselective rhodium-catalyzed coupling of arylboronic acids, 1,3-enynes, and Imines by alkenyl-to-allyl 1,4-rhodium(I) migration. Angewandte Chemie International Edition, 56(51), https://doi.org/10.1002/anie.201709334

A chiral rhodium complex catalyzes the highly enantioselective coupling of arylboronic acids, 1,3-enynes, and imines to give homoallylic sulfamates. The key step is the generation of allylrhodium(I) species by alkenyl-to-allyl 1,4-rhodium(I) migratio... Read More about Enantioselective rhodium-catalyzed coupling of arylboronic acids, 1,3-enynes, and Imines by alkenyl-to-allyl 1,4-rhodium(I) migration.