Sequential processes in palladium-catalyzed silicon-based cross-coupling

Scott E. Denmark, Jack Hung Chang Liu

Research output: Contribution to journalReview article

Abstract

Although developed somewhat later, silicon-based cross-coupling has become a viable alternative to the more conventional Suzuki-Miyaura, Stille-Kosugi-Migita, and Negishi cross-coupling reactions because of its broad substrate scope, high stability of silicon-containing reagents, and low toxicity of waste streams. An empowering and yet underappreciated feature unique to silicon-based cross-coupling is the wide range of sequential processes available. In these processes, simple precursors are first converted to complex silicon-containing cross-coupling substrates, and the subsequent silicon-based cross-coupling reaction affords an even more highly functionalized product in a stereoselective fashion. In so doing, structurally simple and inexpensive starting materials are quickly transformed into value-added and densely substituted products. Therefore, sequential processes are often useful in constructing the carbon backbones of natural products. In this review, studies of sequential processes involving silicon-based cross-coupling are discussed. Additionally, the total syntheses that utilize these sequential processes are also presented.

Original languageEnglish (US)
Pages (from-to)577-587
Number of pages11
JournalIsrael Journal of Chemistry
Volume50
Issue number5-6
DOIs
StatePublished - Dec 2010

Keywords

  • cross-coupling
  • homogeneous catalysis
  • palladium
  • sequential processes
  • silicon

ASJC Scopus subject areas

  • Chemistry(all)

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