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Now showing items 1 - 16 of 3776

  • Gary A. Molander

    Molander   Gary A.  

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  • Haloselective Cross-Coupling via Ni/Photoredox Dual Catalysis

    Kingson Lin   Rebecca J. Wiles   Christopher B. Kelly   Geraint H. M. Davies   Gary A. Molander  

    The chemoselective functionalization of polyfunctional aryl linchpins is crucial for rapid diversification. Although well-explored for Csp2 and Csp nucleophiles, the chemoselective introduction of Csp3 groups remains notoriously difficult and is virtually undocumented using Ni catalysts. To fill this methodological gap, a “haloselective” cross-coupling process of arenes bearing two halogens, I and Br, using ammonium alkylbis(catecholato)silicates, has been developed. Utilizing Ni/photoredox dual catalysis, Csp3–Csp2 bonds can be forged selectively at the iodine-bearing carbon of bromo(iodo)arenes. The described high-yielding, base-free strategy accommodates various protic functional groups. Selective electrophile activation enables installation of a second Csp3 center and can be done without the need for purification of the intermediate monoalkylated product.
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  • Synthesis and Minisci Reactions of Organotrifluoroborato Building Blocks

    Marc Presset   Nicolas Fleury-Brégeot   Daniel Oehlrich   Frederik Rombouts   Gary A. Molander  

    Copper-catalyzed borylation of a variety of organic halides with bis(pinacolato)diboron allows the preparation of diverse potassium organotrifluoroborates. The reactions are mild and general, providing access to a variety of interesting, boron-containing building blocks, including those containing piperidine, pyrrole, azetidine, tetrahydropyran and oxetane substructures. Representative Minisci reactions are reported for select examples.
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  • Base-Free Photoredox/Nickel Dual-Catalytic Cross-Coupling of Ammonium Alkylsilicates

    Matthieu Jouffroy   David N. Primer   Gary A. Molander  

    Single-electron transmetalation is recognized as an enabling technology for the mild transfer of alkyl groups to transition metal catalysts in cross-coupling reactions. Hypercoordinate silicates represent a new and improved class of radical precursors because of their low oxidation potentials and the innocuous byproducts generated upon oxidation. Herein, we report the cross-coupling of secondary and primary ammonium alkylsilicates with (hetero)aryl bromides in good to excellent yields. The base-free conditions have exceptional protic group tolerance on both partners, permitting the cross-coupling of unprotected primary and secondary amines.
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  • Amide-Forming Ligation of Acyltrifluoroborates and Hydroxylamines in Water**

    Aaron M. Dumas   Gary A. Molander   Jeffrey W. Bode  

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  • Synthesis of the stereogenic triad of the halicyclamine A core

    Gary A. Molander   Frédéric Cadoret  

    We describe herein our progress toward the synthesis of halicyclamine A, which possesses very interesting biological activities and has never been synthesized. For this purpose, we proposed a stereoselective Diels-Alder reaction as a key step for the establishment of the stereogenic triad of the bis(piperidinyl) core of this molecule. A series of NMR studies was then conducted to establish the correct stereochemical assignment subsequent to the Diels-Alder reaction. (C) 2010 Elsevier Ltd. All rights reserved.
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  • Synthesis and Cross-coupling of Sulfonamidomethyltrifluoroborates

    Gary A. Molander   Nicolas Fleury-Brégeot  

    Sulfonamidomethyltrifluoroborates were successfully synthesized and cross-coupled with a wide range of aryl and heteroaryl chlorides, allowing the construction of a sulfonamidomethyl aryl linkage through a new disconnection, thus offering a new way to access such structurally interesting motifs.
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  • ChemInform Abstract: Oxidation of Organotrifluoroborates via Oxone.

    Gary A. Molander   Livia N. Cavalcanti  

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  • Azaborininones: Synthesis and Structural Analysis of a Carbonyl-Containing Class of Azaborines

    Geraint H. M. Davies   Asma Mukhtar   Borna Saeednia   Fatemeh Sherafat   Christopher B. Kelly   Gary A. Molander  

    An approach to access azaborininones (carbonyl-containing, boron-based heterocyclic scaffolds) using simple reagents and conditions from both organotrifluoroborates and boronic acids is described. An inexpensive, common reagent, SiO2, was found to serve as both a fluorophile and desiccant to facilitate the annulation process across three different azaborininone platforms. Computational analysis of some of the cores synthesized in this study was undertaken to compare the azaborininones with the analogous carbon-based heterocyclic systems. Computationally derived pKa values, NICS aromaticity calculations, and electrostatic potential surfaces revealed a unique isoelectronic/isostructural relationship between these azaborines and their carbon isosteres that changed based on boron connectivity. Correlation to experimentally derived data supports the computational findings.
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  • Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis

    Camille Remeur   Christopher B. Kelly   Niki R. Patel   Gary A. Molander  

    A protocol for the aminomethylation of aryl halides using α-silylamines via Ni/photoredox dual catalysis is described. The low oxidation potential of these silylated species enables facile single electron transfer (SET) oxidation of the amine followed by rapid desilylation. The resulting α-amino radicals can be directly funneled into a nickel-mediated cross-coupling cycle with aryl halides. The process accomplishes aminomethylation under remarkably mild conditions and tolerates numerous aryl- and heteroaryl halides with an array of functional groups.
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  • Condensation Reactions to Form Oxazoline-Substituted Potassium Organotrifluoroborates

    Gary A. Molander   Wilma Febo-Ayala   Ludivine Jean-Gérard  

    A library of oxazoline-substituted potassium organotrifluoroborates was prepared via the condensation of various potassium formyl-substituted aryl- and heteroaryltrifluoroborates with tosylmethyl isocyanide under basic conditions. The efficient Suzuki-Miyaura cross-coupling of products thus formed to an aryl bromide was achieved in good yield. The method allows the facile preparation of oxazole-containing triaromatic products in two steps from simple potassium formyl-substituted aryl- or heteroaryltrifluoroborates.
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  • Ozonolysis of Unsaturated Organotrifluoroborates.

    Gary A. Molander   David J. Cooper  

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  • ChemInform Abstract: Activation of Si—Si Bonds for Copper(I)-Catalyzed Conjugate Silylation.

    Laura Iannazzo   Gary A. Molander  

    Alkylsilanes are prepared through copper(I)-catalyzed conjugate addition of disilanes to activated alkenes containing sulfono, cyano, and amido groups.
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  • ChemInform Abstract: Metal-Free Chlorodeboronation of Organotrifluoroborates.

    Gary A. Molander   Livia N. Cavalcanti  

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  • Organotrifluoroborates: Expanding Organoboron Chemistry

    Gary A. Molander   Ruth Figueroa  

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  • Oxidation of Hydroxyl-Substituted Organotrifluoroborates.

    Gary A. Molander   Daniel E. Petrillo  

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