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Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Hydrophosphination using [GeCl{N(SiMe3)2}3] as a pre-catalyst.

A N Barrett1, H J Sanderson1, M F Mahon1

  • 1Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK. r.l.webster@bath.ac.uk.

Chemical Communications (Cambridge, England)
|October 15, 2020
PubMed
Summary
This summary is machine-generated.

Researchers report the first germanium-catalyzed hydrophosphination reaction. This novel method efficiently produces anti-Markovnikov products from diphenylphosphine and unsaturated compounds at room temperature.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Germanium catalysis is underexplored, with limited examples in organic transformations.
  • Existing germanium-catalyzed reactions primarily include polymerization and hydroboration.

Purpose of the Study:

  • To introduce the first germanium-catalyzed hydrophosphination reaction.
  • To explore the utility of germanium pre-catalysts in novel bond-forming reactions.

Main Methods:

  • Reaction of diphenylphosphine with styrenes or internal alkynes.
  • Utilizing a germanium pre-catalyst under mild conditions.
  • Characterization of the resulting anti-Markovnikov products.

Main Results:

  • Successful demonstration of the first hydrophosphination catalyzed by germanium.
  • Achieved anti-Markovnikov regioselectivity in the addition of diphenylphosphine.
  • The reaction proceeds efficiently at room temperature.

Conclusions:

  • Germanium pre-catalysts can effectively mediate hydrophosphination reactions.
  • This work expands the scope of germanium-catalyzed organic transformations.
  • The developed method offers a new route to anti-Markovnikov functionalized molecules.