Pd(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol via a Chiral Auxiliary.

We report the development of palladium(0)-catalyzed syn -selective 1,2-carboboration and -silylation reactions of alkenes containing cleavable directing groups. With B 2 pin 2 or PhMe 2 Si-Bpin as nucleophiles and aryl/alkenyl triflates as electrophiles, a broad range of mono-, di-, tri- and tetrasubstituted alkenes are compatible in these transformations. We further describe a directed dearomative 1,2-carboboration of electron-rich heteroarenes by employing this approach. Through use of a removable chiral directing group, we demonstrate the viability of achieving stereoinduction in Heck-type alkene 1,2-difunctionalization. This work introduces new avenues to access highly functionalized boronates and silanes with precise regioand stereocontrol.

• Publication year

  2019

• Venue

  Angewandte Chemie

• Publication date

  2019-11-18

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/anie.201910304PMID 31538388PMCID PMC7337986
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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