An intermolecular coupling between sulfoximines and allyl amines, linked to the picolinamide directing group, is developed by leveraging a nucleopalladation-guided regioselective hydroamination strategy, enabling the production of a range of valuable -alkyl sulfoximines in high yields. The protocol features operational simplicity and a broad substrate scope and was also amenable to aniline nucleophiles. Synthetic utilities were showcased through scale-up reactions and product diversifications, leading to biorelevant molecules.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.orglett.5c00316 | DOI Listing |
Org Lett
February 2025
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui South Road, Lanzhou 730000, China.
Herein, we report a visible-light-driven and cobalt-mediated 1,4-hydroamination reaction of 1,3-dienes with arylmines as the nucleophiles. The reaction involves regioselective addition of [Co]-H to 1,3-diene, followed by oxidation and nucleophilic substitution by amines. Using Ir(ppy) as the photocatalyst enables the cobalt redox cycle to be implemented without using an external oxidant and hydride regent.
View Article and Find Full Text PDFOrg Lett
February 2025
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, Tamil Nadu, India.
An intermolecular coupling between sulfoximines and allyl amines, linked to the picolinamide directing group, is developed by leveraging a nucleopalladation-guided regioselective hydroamination strategy, enabling the production of a range of valuable -alkyl sulfoximines in high yields. The protocol features operational simplicity and a broad substrate scope and was also amenable to aniline nucleophiles. Synthetic utilities were showcased through scale-up reactions and product diversifications, leading to biorelevant molecules.
View Article and Find Full Text PDFOrg Lett
February 2025
Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China.
In this study, we describe a generally straightforward methodology for the catalytic synthesis of chiral aminopiperidine from pyridine and azoles. The key step was the palladium-catalyzed regioselective N-H insertion into the double bond of 1,2-dihydropyridine. This hydroamination exhibits a wide substrate scope and functional group compatibility.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Instituto Universitario de Tecnología Química, Universitat Politècnica de València-Consejo Superior de Investigaciones Científicas, Universitat Politècnica de València, Av. De los Naranjos s/n, 46022 Valencia, Spain.
Due to their conductive properties and optoelectronic tunability, MXenes have revolutionized the area of electrocatalysis and active materials in supercapacitors. In comparison, there are only a few reports on MXenes as thermal catalysts for general organic reactions. Herein, the unprecedented catalytic activity of TiC MXene for the hydroamination of alkynes is reported, overcoming the limitations of poor activity, lack of selectivity, and stability, which are generally encountered in the solid catalysts known so far.
View Article and Find Full Text PDFJ Org Chem
January 2025
School of Chemistry, IGCME, The Key Laboratory of Low-Carbon Chemistry & Energy Conservation of Guangdong Province, Guangdong Provincial Key Laboratory of Chiral Molecules and Drug Discovery, Sun Yat-sen University, Guangzhou 510006, People's Republic of China.
The ligand-free Lewis acid-mediated regioselective hydroamination and hydroarylation of styrenes have been successfully developed in the presence of isatins or heterocyclic aryl compounds such as benzothiophenes and benzofurans. The reactions tolerate a variety of functional groups and afford the corresponding products in moderate to good yields. Deuterium labeling experiments show that the functionalized hydrogen of styrenes was derived from the nitrogen-hydrogen of the substrates in the hydroamination.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!