Outputs (27)

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.

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.