Late-stage C–H functionalization of azines

CM Josephitis, HMH Nguyen, A McNally - Chemical reviews, 2023 - ACS Publications
Azines, such as pyridines, quinolines, pyrimidines, and pyridazines, are widespread
components of pharmaceuticals. Their occurrence derives from a suite of physiochemical …

Palladium-Catalyzed Enantioselective β-C(sp3)–H Activation Reactions of Aliphatic Acids: A Retrosynthetic Surrogate for Enolate Alkylation and Conjugate Addition

EL Lucas, NYS Lam, Z Zhuang, HSS Chan… - Accounts of chemical …, 2022 - ACS Publications
Conspectus Enolate alkylation and conjugate addition into an α, β-unsaturated system have
served as long-standing strategic disconnections for the installation of α-or β-substituents on …

A perspective on late-stage aromatic C–H bond functionalization

L Zhang, T Ritter - Journal of the American Chemical Society, 2022 - ACS Publications
Late-stage functionalization of C–H bonds (C–H LSF) can provide a straightforward
approach to the efficient synthesis of functionalized complex molecules. However, C–H LSF …

Ligand-controlled divergent dehydrogenative reactions of carboxylic acids via C–H activation

Z Wang, L Hu, N Chekshin, Z Zhuang, S Qian, JX Qiao… - Science, 2021 - science.org
Dehydrogenative transformations of alkyl chains to alkenes through methylene carbon-
hydrogen (C–H) activation remain a substantial challenge. We report two classes of pyridine …

Catalyst-controlled site-selective methylene C–H lactonization of dicarboxylic acids

HSS Chan, JM Yang, JQ Yu - Science, 2022 - science.org
Catalyst-controlled site-selective activation of β-and γ-methylene carbon-hydrogen (C–H)
bonds of free carboxylic acids is a long-standing challenge. Here we show that, with a pair of …

C(sp2)–H Hydroxylation via Catalytic 1,4-Ni Migration with N2O

H Zhang, J Rodrigalvarez, R Martin - Journal of the American …, 2023 - ACS Publications
Herein, we report a Ni-catalyzed C (sp2)–H hydroxylation of aryl bromides with N2O as an
oxygen-atom donor. The reaction is enabled by a 1, 4-Ni translocation that results in …

Ligand-Enabled C–H Hydroxylation with Aqueous H2O2 at Room Temperature

Z Li, HS Park, JX Qiao, KS Yeung… - Journal of the American …, 2022 - ACS Publications
With the large number of Pd (II)-catalyzed C–H activation reactions of native substrates
developed in the past decade, the development of catalysts to enable the use of green …

Hydrogen-bond-acceptor ligands enable distal C(sp3)–H arylation of free alcohols

DA Strassfeld, CY Chen, HS Park, DQ Phan, JQ Yu - Nature, 2023 - nature.com
The functionalization of C–H bonds in organic molecules is one of the most direct
approaches for chemical synthesis. Recent advances in catalysis have allowed native …

Iron-catalyzed hydrobenzylation: stereoselective synthesis of (−)-eugenial C

X Gan, S Kotesova, A Castanedo… - Journal of the …, 2023 - ACS Publications
Metal-hydride hydrogen atom transfer (MHAT) has emerged as a useful tool to form
quaternary carbons from alkenes via hydrofunctionalization. Methods to date that cross …

Anaerobic Hydroxylation of C(sp3)–H Bonds Enabled by the Synergistic Nature of Photoexcited Nitroarenes

JM Paolillo, AD Duke, ES Gogarnoiu… - Journal of the …, 2023 - ACS Publications
A photoexcited-nitroarene-mediated anaerobic C–H hydroxylation of aliphatic systems is
reported. The success of this reaction is due to the bifunctional nature of the photoexcited …