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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
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Introduction
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In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...
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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid.

Daniel J Scott1, Nicholas A Phillips1, Joshua S Sapsford1

  • 1Department of Chemistry, Imperial College London, London, SW7 2AZ, UK.

Angewandte Chemie (International Ed. in English)
|October 25, 2016
PubMed
Summary

This study introduces a new tin-based Lewis acid for frustrated Lewis pair (FLP) chemistry, enabling efficient catalytic hydrogenation of diverse unsaturated compounds with enhanced stability and moisture tolerance.

Keywords:
catalysisfrustrated Lewis pairshydrogenationstannyliumtin

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Main-Group Chemistry

Background:

  • Frustrated Lewis pair (FLP) chemistry has advanced significantly, but its use in hydrogenation is limited to specific early main-group Lewis acids.
  • Existing Lewis acids (LAs) restrict reactivity, substrate scope, and stability in FLP applications.

Purpose of the Study:

  • To introduce and investigate a novel, alternative Lewis acid for FLP-mediated H2 activation and catalytic hydrogenation.
  • To overcome the limitations associated with traditional boron-based LAs in FLP chemistry.

Main Methods:

  • Synthesis of iPr3SnOTf as a surrogate for the trialkylstannylium ion.
  • Evaluation of FLP-mediated H2 activation and catalytic hydrogenation using the new tin-based LA.
  • Testing substrate scope and stability under various conditions, including moisture tolerance.

Main Results:

  • iPr3SnOTf effectively mediates H2 activation and catalytic hydrogenation.
  • Demonstrated competence in hydrogenating various unsaturated functional groups, a unique capability for non-boron main-group FLP LAs.
  • Exhibited high thermal robustness and remarkable moisture tolerance.

Conclusions:

  • iPr3SnOTf represents a versatile and robust alternative Lewis acid for frustrated Lewis pair chemistry.
  • This development expands the scope of FLP applications in catalytic hydrogenation, offering improved reactivity and stability.