Anion relay chemistry: Access to the type II ARC reaction manifold through a fundamentally different reaction pathway exploiting 1-oxa-2-silacyclopentanes and related congeners

Amos B. Smith*, Rongbiao Tong, Won Suk Kim, William A. Maio

*Corresponding author for this work

Research output: Contribution to journalJournal Articlepeer-review

34 Citations (Scopus)

Abstract

Distinctly different: Two 1-oxa-2-silacyclopentenes and a saturated congener have been synthesized and demonstrated to provide access to type II anion relay chemistry (ARC) through a fundamentally new mechanistic pathway. Similar to previous studies, but contrary to initial hypothesis, Brook rearrangement additives (hexamethylphosphoramide and CuI) are necessary to promote Si migration and anion capture.

Original languageEnglish
Pages (from-to)8904-8907
Number of pages4
JournalAngewandte Chemie - International Edition
Volume50
Issue number38
DOIs
Publication statusPublished - 12 Sept 2011
Externally publishedYes

Keywords

  • Brook rearrangement
  • alkylating desilylation
  • anion relay chemistry
  • cross coupling
  • siloxanes

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