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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.