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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
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Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Beyond Dehydrocoupling: Group 2 Mediated Boron-Nitrogen Desilacoupling.

David J Liptrot1, Merle Arrowsmith1, Annie L Colebatch1

  • 1Department of Chemistry, University of Bath, Bath BA2 7AY (UK).

Angewandte Chemie (International Ed. in English)
|October 17, 2015
PubMed
Summary
This summary is machine-generated.

Alkaline-earth bis(trimethylsilyl)amides catalyze boron-nitrogen bond formation via desilacoupling. This novel main-group coupling avoids hydrogen gas elimination, yielding silylhydrides.

Keywords:
calciumdehydrocouplingdesilacouplingmagnesiumstrontium

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Main-Group Chemistry

Background:

  • Boron-nitrogen bonds are crucial in materials science and pharmaceuticals.
  • Previous methods for B-N bond formation often require harsh conditions or produce hazardous byproducts.
  • Catalytic main-group element-element coupling reactions are less explored than their transition metal counterparts.

Purpose of the Study:

  • To develop novel precatalysts for efficient boron-nitrogen bond formation.
  • To investigate a new catalytic main-group element-element coupling reaction.
  • To explore the reactivity of alkaline-earth bis(trimethylsilyl)amides in organic synthesis.

Main Methods:

  • Synthesis and characterization of alkaline-earth bis(trimethylsilyl)amide complexes [Ae{N(SiMe3 )2 }2 (thf)2 ] (Ae=Mg, Ca, Sr).
  • Testing these complexes as precatalysts in the desilacoupling reaction of amines (RR'NH) with pinBSiMe2 Ph.
  • Analysis of reaction products, including the identification of Me2 PhSiH.

Main Results:

  • The alkaline-earth complexes effectively catalyzed the formation of boron-nitrogen bonds.
  • The reaction proceeded via a desilacoupling mechanism, cleaving the Si-N bond.
  • A stoichiometric amount of Me2 PhSiH was produced, and no H2 elimination was observed.
  • This represents the first catalytic main-group element-element coupling reaction not reliant on H2 elimination.

Conclusions:

  • Alkaline-earth bis(trimethylsilyl)amides are highly effective precatalysts for B-N bond formation.
  • The developed catalytic system offers a novel and efficient route for synthesizing organoboron and organosilicon compounds.
  • This work expands the scope of main-group catalysis and provides a unique pathway for element-element bond formation.