The Experts below are selected from a list of 133377 Experts worldwide ranked by ideXlab platform
Mikhail S Nechaev - One of the best experts on this subject based on the ideXlab platform.
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stannylation of aryl halides stille Cross Coupling and one pot two step stannylation stille Cross Coupling reactions under solvent free conditions
European Journal of Organic Chemistry, 2018Co-Authors: Pavel S Gribanov, Yulia D Golenko, Maxim A Topchiy, Lidiya I Minaeva, Andrey F Asachenko, Mikhail S NechaevAbstract:Solvent-free protocols for palladium-catalyzed stannylation of aryl halides, Stille Cross-Coupling, and one-pot two-step stannylation/Stille Cross-Coupling (SSC) are reported for the first time. (Het)aryl halides bearing acceptor, donor, as well as sterically demanding substituents are stannylated and/or coupled in high yields. The reactions are catalyzed by conventional palladium(II) acetate/PCy3 (Pd(OAc)2/PCy3) under air, using available base CsF, and without the use of high purity reagents. The developed synthetic procedures are versatile, robust, and easily scalable. The absence of solvent, and the elimination of isolation procedures of aryl stannanes makes SSC protocol simple, step economical, and highly efficient for the synthesis of biaryls via one-pot two-step procedure.
Pavel S Gribanov - One of the best experts on this subject based on the ideXlab platform.
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stannylation of aryl halides stille Cross Coupling and one pot two step stannylation stille Cross Coupling reactions under solvent free conditions
European Journal of Organic Chemistry, 2018Co-Authors: Pavel S Gribanov, Yulia D Golenko, Maxim A Topchiy, Lidiya I Minaeva, Andrey F Asachenko, Mikhail S NechaevAbstract:Solvent-free protocols for palladium-catalyzed stannylation of aryl halides, Stille Cross-Coupling, and one-pot two-step stannylation/Stille Cross-Coupling (SSC) are reported for the first time. (Het)aryl halides bearing acceptor, donor, as well as sterically demanding substituents are stannylated and/or coupled in high yields. The reactions are catalyzed by conventional palladium(II) acetate/PCy3 (Pd(OAc)2/PCy3) under air, using available base CsF, and without the use of high purity reagents. The developed synthetic procedures are versatile, robust, and easily scalable. The absence of solvent, and the elimination of isolation procedures of aryl stannanes makes SSC protocol simple, step economical, and highly efficient for the synthesis of biaryls via one-pot two-step procedure.
John Montgomery - One of the best experts on this subject based on the ideXlab platform.
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Regioselective Allene Hydroarylation via One-Pot Allene Hydrosilylation/Pd-Catalyzed Cross-Coupling
2016Co-Authors: Zachary D Miller, John MontgomeryAbstract:ABSTRACT: Advances in hydroarylation have been achieved by the development of a one-pot regioselective allene hydrosilylation/Pd(0)-catalyzed Cross-Coupling protocol. The regioselectivity is primarily governed by N-heterocyclic carbene (NHC) ligand identity in the hydrosilylation step and is preserved in the subsequent Cross-Coupling reaction. This methodology affords streamlined access to functionalized 1,1-disubstituted alkenes with excellent regiocontrol. Alkenylsilanes are versatile nucleophiles in metal-catalyzedCross-Coupling reactions. Numerous carbon−carbon bond-forming reactions with alkenylsilanes have been well developed,1 including the powerful Cross-Coupling methodology extensively developed by Hiyama and Denmark.2−4 Currently, the most direct routes to alkenylsilanes are via metal-catalyzed hydro-silylations of alkynes.5 However, subtle alterations in the π-component, silane Coupling partner, and metal catalyst often have substantial effects on the reaction outcome, leading t
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regioselective allene hydroarylation via one pot allene hydrosilylation pd catalyzed Cross Coupling
Organic Letters, 2014Co-Authors: Zachary D Miller, John MontgomeryAbstract:Advances in hydroarylation have been achieved by the development of a one-pot regioselective allene hydrosilylation/Pd(0)-catalyzed Cross-Coupling protocol. The regioselectivity is primarily governed by N-heterocyclic carbene (NHC) ligand identity in the hydrosilylation step and is preserved in the subsequent Cross-Coupling reaction. This methodology affords streamlined access to functionalized 1,1-disubstituted alkenes with excellent regiocontrol.
Mark R Biscoe - One of the best experts on this subject based on the ideXlab platform.
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stereospecific pd catalyzed Cross Coupling reactions of secondary alkylboron nucleophiles and aryl chlorides
Journal of the American Chemical Society, 2014Co-Authors: Shibin Zhao, Amruta Joshipangu, Mohamed Diane, Mark R BiscoeAbstract:We report the development of a Pd-catalyzed process for the stereospecific Cross-Coupling of unactivated secondary alkylboron nucleophiles and aryl chlorides. This process tolerates the use of secondary alkylboronic acids and secondary alkyltrifluoroborates and occurs without significant isomerization of the alkyl nucelophile. Optically active secondary alkyltrifluoroborate reagents undergo Cross-Coupling reactions with stereospecific inversion of configuration using this method.
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stereoretentive pd catalysed stille Cross Coupling reactions of secondary alkyl azastannatranes and aryl halides
Nature Chemistry, 2013Co-Authors: Chaoyuan Wang, Rongcai Huang, Mark R BiscoeAbstract:A general method for the stereoretentive Pd-catalysed Cross-Coupling of secondary alkyl azastannatranes and aryl electrophiles is described. This work constitutes the first example of a stereoretentive Cross-Coupling reaction using an unactivated, isolable, optically active organometallic nucleophile.
Michal Szostak - One of the best experts on this subject based on the ideXlab platform.
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2 methyltetrahydrofuran a green solvent for iron catalyzed Cross Coupling reactions
Chemsuschem, 2018Co-Authors: Elwira Bisz, Michal SzostakAbstract:Iron-catalyzed Cross-Coupling reactions allow sustainable formation of C-C bonds using cost-effective, earth-abundant base-metal catalysis for complex syntheses of pharmaceuticals, natural products, and fine chemicals. The major challenge to maintain full sustainability of the process is the identification of green and renewable solvents that can be harnessed to replace the conventional solvents for this highly attractive reaction. Herein, iron-catalyzed Cross-Coupling of aryl chlorides and tosylates with challenging organometallic reagents possessing β-hydrogens is found to proceed in good to excellent yields with the green, sustainable, and eco-friendly 2-methyltetrahydrofuran (2-MeTHF) as solvent. The reaction operates with excellent functional group tolerance under very mild conditions. Furthermore, large-scale Cross-Coupling, Cross-Coupling of heteroaromatic substrates, and Cross-Coupling of challenging aryl tosylates and carbamates mediated by Fe-N-heterocyclic carbene catalytic systems in eco-friendly 2-MeTHF were also carried out. The developed method was applied to the key Cross-Coupling in the synthesis of a fibrinolysis inhibitor, further highlighting the potential of 2-MeTHF as a general solvent for sustainable iron-catalyzed Cross-Coupling reactions.
