Herein, we report an inexpensive first-row transition metal Ni heterogeneous catalytic system for the C -mono alkylation of fluorene using alcohols as alkylating agents via borrowing hydrogen strategy. The catalytic protocol displayed versatility with high yields of the desired products using various types of primary alcohols, including aryl/hetero aryl methanols, and aliphatic alcohols as alkylating agents. The catalyst Ni NPs@N-C was synthesized via high-temperature pyrolysis strategy, using ZIF-8 as the sacrificial template. The Ni NPs@N-C catalyst was characterized by XPS, HR-TEM, HAADF-STEM, XRD and ICP-MS. The catalyst is stable even in the air at room temperature, displayed excellent activity and could be recycled 5 times without appreciable loss of its activity.
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http://dx.doi.org/10.1002/asia.202400989 | DOI Listing |
Nat Chem
January 2025
Department of Chemistry, Scripps Research, La Jolla, CA, USA.
Amino alcohols are vital in natural products, pharmaceuticals and agrochemicals, and as key building blocks for various applications. Traditional synthesis methods often rely on polar bond retrosynthetic analysis, requiring extensive protecting group manipulations that complicate direct access. Here we show a streamlined approach using a serine-derived chiral carboxylic acid in stereoselective electrocatalytic decarboxylative transformations, enabling efficient access to enantiopure amino alcohols.
View Article and Find Full Text PDFAlzheimers Dement
December 2024
Yale University, New Haven, CT, USA.
Background: Alcohol Use Disorder (AUD) affects over 15 million individuals in the United States, contributing to oxidative stress, neuroinflammation, and elevating the risk of neurodegeneration. Despite this, the connection between AUD and aging conditions, particularly Alzheimer's disease (AD), remains unclear. AD, with a heritability of 60-80%, is genetically linked, necessitating an exploration of the molecular implications of AUD and genetic susceptibility to AD.
View Article and Find Full Text PDFThe development of new protocols for stereospecific and stereoselective halogenation transformations by mild reaction conditions is a highly desirable research target for the chemical and pharmaceutical industries. Following the straightforward methodology for directly transforming a wide scope of alcohols to alkyl bromides and chlorides using substoichiometric amounts of thioureas and N-halo succinimides (NXS) as a halogen source in a single step, we noticed that in apolar solvents bromination of chiral secondary alcohols did not produce the expected racemates. In this study, the stereochemical aspects of the bromination reaction were examined.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of Chemistry, University of Calcutta, 92, A. P. C. Road, Kolkata - 700 009, West Bengal, India.
In this study, we have investigated the reactivity of thioamides with alcohols by utilizing HPO as a low-toxicity, cost-effective Brønsted acid catalyst. This report includes a methodology for the synthesis of thioesters from thioamides and 2-hydroxyaryl alcohols. Thioesters are emerging as a notable class of organic molecules due to their biological relevance, extensive use in drug discovery, and industrial applications.
View Article and Find Full Text PDFNat Commun
December 2024
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China.
The functionalized polycycle with densely contiguous tertiary stereocenters is a formidable challenge in synthesizing the parvistemoline family of Stemona alkaloids. We herein report their catalytic, asymmetric total syntheses in 13-14 steps from commercially available 2-(methoxycarbonyl)-pyrrole, featuring the development and deployment of an Ir/Pd-synergistically-catalyzed allylation of α-non-substituted keto esters with secondary aryl-substituted alcohols, stereodivergently accessible to four stereoisomers. Using chiral Pd-enolate and Ir π-allyl complex under neutral conditions, no epimerization occurs.
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