The amide-directed cobalt(III)-catalyzed C-H amidation of ferrocene carboxamides using 1,4,2-dioxazol-5-ones as robust and efficient amidating reagents has been developed. This reaction proceeds efficiently under mild reaction conditions with good functional group tolerance, providing expedient access to a broad range of ferrocenes containing a nitrogen group on the Cp ring.
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http://dx.doi.org/10.1021/acs.orglett.8b03938 | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084, China.
Enantioselective hydrogenation of tetrasubstituted alkenes to form 1,2-contiguous stereocenters is a particularly appealing but highly challenging transformation in asymmetric catalysis. Despite the notable progress achieved in enantioselective hydrogenation over the past decades, enantioselective hydrogenation of all-carbon tetrasubstituted alkenes containing multiple alkyl groups remains an unsolved challenge. Here, we report a rhodium-catalyzed highly diastereo- and enantioselective hydrogenation of diverse acyclic multisubstituted alkenes under mild conditions.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, Malaviya National Institute of Technology Jaipur, JLN Marg, Jaipur 302017, Rajasthan, India.
A selective -olefination of primary amides yields valuable motifs for pharmaceuticals. Primary amide-directed -olefination of benzamide using unactivated alkenes was successfully conducted with a ruthenium(II) catalyst. The established protocol demonstrates efficacy across various benzamides, achieving moderate to good yields with high functional group tolerance.
View Article and Find Full Text PDFOrg Lett
July 2024
Key Laboratory of Xinjiang Native Medicinal and Edible Plant Resource Chemistry, College of Chemistry and Environmental Sciences, Kashi University, Kashgar, Xinjiang 844000, People's Republic of China.
Benzylamines belong to an important class of building blocks in the synthesis of biologically active natural products and drugs. Encumbered by amide-directed -C-H activation, remote -selective C-H functionalization of benzylamines has hitherto not been realized to date. Here, we report a palladium-catalyzed -selective C-H olefination and acetoxylation of benzylamines using a functionalized benzoyl template.
View Article and Find Full Text PDFOrg Lett
March 2024
Tenure-Track Program for Innovative Research, University of Fukui, 3-9-1 Bunkyo, Fukui-shi, Fukui 910-8507, Japan.
We developed a rhodium-catalyzed chain-walking hydrothiolation process for internal alkenes, which offers a novel and efficient alternative for C(sp)-H bond cleavage, while focusing on thiol incorporation. This method exclusively affords ,-acetals at 36-90% yields. Regioconvergent hydrothiolation significantly improved the effectiveness of this transformation.
View Article and Find Full Text PDFJ Am Chem Soc
January 2024
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing 100084, China.
Despite the current progress achieved in asymmetric hydroacylations, highly enantioselective catalytic addition of unfunctionalized aldehydes to internal alkenes remains an unsolved challenge. Here, using a coordination-assisted strategy, we developed a rhodium-catalyzed regio- and enantioselective addition of unfunctionalized aldehydes to internal alkenes such as enamides and β,γ-unsaturated amides. Valuable α-amino ketones and 1,4-dicarbonyl compounds were directly obtained with high enantioselectivity from readily available materials.
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