A Synthetic Pathway to Arylsilyl(silyl)arenes; Selective Si-C Cleavage in Bis(arylsilyl)arenes with Triflic Acid

Robert Schröck, Klaus Angermaier, Hubert Schmidbaur

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

Bis(arylsilyl)arenes such as bis(p-tolylsilyl)benzene and bis(p-anisylsilyl)naphthalene are available from in situ Grignard reactions of the corresponding haloarenes, arylchlorosilanes and magnesium in tetrahydrofuran. Treatment of these products with one equivalent of trifluoromethanesulfonic (triflic) acid at low temperatures leads to arylsilyl(trifluoromethyl-sulfonatosilyl)arenes, which can be converted into arylsilyl(silyl)arenes using LiAlH4. The regioselectivity of the Si-C cleavage is surprisingly high. Any of the first dearylation steps is faster then the consecutive steps. Ortho, meta and para substituted p-tolylsilyl(silyl)benz-enes, 1, 4-dibromo-2-(p-tolylsilyl)-5-(silyl)benzene, and 1-(p-anisylsilyl)-8-(silyl)naphthalene have thus been obtained in good to moderate yields. These compounds can serve as starting materials for monofunctional arylsilanes with a tailored structure. The crystal structure of 1-(p-anisylsiiyl)-8-(silyl)naphthalene has been determined by single crystal X-ray diffraction.

Original languageEnglish
Pages (from-to)613-618
Number of pages6
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume50
Issue number4
DOIs
StatePublished - 1 Apr 1995
Externally publishedYes

Keywords

  • Arylsilyl(silyl)benzenes
  • Arylsilyl(silyl)naphthalenes
  • Silanes
  • Silylbenzenes

Fingerprint

Dive into the research topics of 'A Synthetic Pathway to Arylsilyl(silyl)arenes; Selective Si-C Cleavage in Bis(arylsilyl)arenes with Triflic Acid'. Together they form a unique fingerprint.

Cite this