All Outputs (3)

Copper-Catalyzed Chan–Lam Cyclopropylation of Phenols and Azaheterocycles (2018)
Journal Article
Derosa, J., O’Duill, M. L., Holcomb, M., Boulous, M. N., Patman, R. L., Wang, F., …Engle, K. M. (2018). Copper-Catalyzed Chan–Lam Cyclopropylation of Phenols and Azaheterocycles. Journal of Organic Chemistry, 83(7), 3417-3425. https://doi.org/10.1021/acs.joc.7b03100

Small molecules containing cyclopropane-heteroatom linkages are commonly needed in medicinal chemistry campaigns yet are problematic to prepare using existing methods. To address this issue, a scalable Chan-Lam cyclopropylation reaction using potassi... Read More about Copper-Catalyzed Chan–Lam Cyclopropylation of Phenols and Azaheterocycles.

Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization (2017)
Journal Article
O’Duill, M. L., Matsuura, R., Wang, Y., Turnbull, J. L., Gurak, J. A., Gao, D., …Engle, K. M. (2017). Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization. Journal of the American Chemical Society, 139(44), 15576-15579. https://doi.org/10.1021/jacs.7b08383

Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselectiv... Read More about Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization.

Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl (2017)
Journal Article
Derosa, J., Cantu, A. L., Boulous, M. N., O’Duill, M. L., Turnbull, J. L., Liu, Z., …Engle, K. M. (2017). Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl. Journal of the American Chemical Society, 139(14), 5183-5193. https://doi.org/10.1021/jacs.7b00892

A regioselective anti-hydrochlorination of unactivated alkynes is reported. The reaction utilizes in situ generated HCl as the source of both the Cl - and H + and is catalyzed by palladium(II) acetate, with loadings as low as 25 ppm. Removable picoli... Read More about Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl.