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NHC-Stabilized Silyl-Substituted Chlorosilylene.

Gizem Dübek1, Franziska Hanusch1, Shigeyoshi Inoue1

  • 1Department of Chemistry, Catalysis Research Center and WACKER-Institute of Silicon Chemistry , Technical University of Munich , Lichtenbergstraße 4 , D-85748 Garching , Germany.

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Summary

Researchers synthesized the first N-heterocyclic carbene (NHC) stabilized chlorosilylene. This novel compound, a key intermediate, can form metal complexes and undergo further reactions to create new silicon compounds.

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Area of Science:

  • Organosilicon Chemistry
  • Main Group Chemistry
  • Coordination Chemistry

Background:

  • N-heterocyclic carbenes (NHCs) are versatile ligands in coordination chemistry.
  • Silylenes, silicon analogues of carbenes, are reactive species often stabilized by bulky substituents or ligands.
  • The isolation of low-valent silicon species provides insights into silicon's bonding capabilities.

Purpose of the Study:

  • To synthesize and characterize the first N-heterocyclic carbene (NHC) stabilized silyl-substituted chlorosilylene.
  • To explore the reactivity of this novel chlorosilylene with metal precursors and other reagents.
  • To investigate the potential for generating new classes of silicon compounds.

Main Methods:

  • Selective dehydrochlorination of a silyl-based Si(IV) precursor using an NHC.
  • Reaction of the isolated chlorosilylene with an iron carbonyl dimer to form a metal complex.
  • Chloride/hydride metathesis reactions with the chlorosilylene.
  • Treatment of the chlorosilylene with additional NHC to form silyliumylidene ions.

Main Results:

  • Isolation of the first NHC-stabilized silyl-substituted chlorosilylene (compound 1).
  • Formation of an iron chlorosilylene complex (compound 2) from compound 1.
  • Synthesis of a stable NHC-silylene hydride borane adduct (compound 3) via metathesis.
  • Conversion of compound 1 into silyl-substituted silyliumylidene ions (compound 4) upon reaction with excess NHC.

Conclusions:

  • The successful isolation of NHC-stabilized chlorosilylene demonstrates a new route to stabilize low-valent silicon species.
  • The reactivity studies showcase the versatility of this chlorosilylene as a building block for novel organosilicon compounds and metal complexes.
  • This work expands the scope of known NHC-stabilized silicon compounds and opens avenues for future research in silicon chemistry.