Lewis base-promoted carbon-carbon sp3-sp3 coupling reactions of α-silyl silylethers

Jonathan A. Brekan, Dmitri Chernyak, Kolby L. White, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

A Lewis base-promoted addition of α-silyl silylethers to primary halides has been developed. This new carbon-carbon sp3-sp3 bond-forming process accesses an unconventional reactivity pattern (d 1 synthon) from easily accessible precursors. The strategy accommodates a variety of primary alkyl, allylic and benzylic electrophiles and α-silyl silylethers. These d1 synthons have also been used in the synthesis of cross pinacol and benzil products. Mechanistic studies indicate significant intermolecular silyl group exchange during the reaction.

Original languageEnglish (US)
Pages (from-to)1205-1210
Number of pages6
JournalChemical Science
Volume3
Issue number4
DOIs
StatePublished - Apr 2012

ASJC Scopus subject areas

  • Chemistry(all)

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