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Nickel-Catalyzed Reductive Alkenylation of Enol Derivatives: A Versatile Tool for Alkene Construction.
Acc Chem Res
November 2024
State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou 730000, China.
Article Synopsis
- - Ketone-to-alkene transformations are important in organic chemistry, and recent nickel-catalyzed reductive alkenylation reactions show promise for creating a variety of alkenes using different functional groups.
- - The authors' research started with coupling α-chloroboronates, then expanded to include a range of radical-inactive compounds, leading to the development of new strategies for cross-selectivity in various chemical reactions.
- - These advancements enable efficient synthesis of valuable products, including functionalized cycloalkenes and diverse alkenes, by broadening the types of enol derivatives used in the reactions, making the approach more accessible and practical.
The addition of phosphines (PR) to Michael acceptors is a key step in many Lewis-base catalysed reactions. The kinetics of the reactions of ten phosphines with ethyl acrylate, ethyl allenoate, ethyl propiolate, ethenesulfonyl fluoride, and ethyl 2-butynoate in dichloromethane at 20 °C was followed by photometric and NMR spectroscopic methods. The experimentally determined second-order rate constants show that electronic effects in sterically unencumbered phosphines affect their nucleophilicity towards different classes of Michael acceptors in the same ordering.
View Article and Find Full Text PDFFriedel-Crafts Reactivity with Sulfondiimidoyl Fluorides for the Synthesis of Heteroaryl Sulfondiimines.
Angew Chem Int Ed Engl
October 2024
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK.
Sulfur functional groups are ubiquitous in molecules used in the pharmaceutical and agrochemical industries, and within these collections sulfones hold a prominent position. The double aza-analogues of sulfones, sulfondiimines, offer significant potential in discovery chemistry but to date their applications have been limited by the lack of convenient synthetic routes. The existing methods mainly rely on imination of low-valent-sulfur intermediates, or the combination of pre-formed organometallic reagents and electrophilic S(VI)-functionalities.
View Article and Find Full Text PDFTowards Nickel-NHC Fluoro Complexes-Synthesis of Imidazolium Fluorides and Their Reactions with Nickelocene.
Molecules
September 2024
Organometallic Research Group (OMCAT), LIMA CNRS UMR 7042, ECPM, University of Strasbourg, 25 rue Becquerel, 67087 Strasbourg, France.
While hundreds of complexes of the general formula [Ni(η-CH)(NHC)(X)] exist (NHC = a N-heterocyclic carbene, X = Cl, Br, I), none is yet known with X = F. We attempted to prepare such a species by reacting nickelocene with imidazolium fluorides. Three imidazolium fluorides (ImH) F [Im = (,'-(R)-imidazolium: , IMe, R = Me; , IMes, R = 2,4,6-trimethylphenyl; , IPr, R = 2,6-diisopropylphenyl)] were prepared and characterized by spectroscopic methods.
View Article and Find Full Text PDFThionyl fluoride as a sulfur(IV) SuFEx hub for the efficient syntheses of sulfinamides and sulfinate esters.
Chem Commun (Camb)
September 2024
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.
Herein, we demonstrate a method for the syntheses of sulfinamides and sulfinate esters using a novel sulfur(IV) fluoride exchange reaction with organometallic reagents. Our strategy involves the addition of an amine or alcohol nucleophile to thionyl fluoride, acting as a S(IV) SuFEx hub, followed by an organometallic reagent. This approach allows efficient access to sulfinamides (45-91% yields) and sulfinate esters (44-82% yields) in only 30 minutes.
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