Catalytic Access to Diastereometrically Pure Four- and Five-Membered Silyl-Heterocycles Using Transborylation

Dominic R. Willcox*, Emanuele Cocco, Gary S. Nichol, Armando Carlone, Stephen P. Thomas*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

Silyl-heterocycles offer a unique handle to expand and explore chemical space, reactivity, and functionality. The shortage of catalytic methods for the preparation of diverse and functionalized silyl-heterocycles however limits widespread exploration and exploitation. Herein the borane-catalyzed intramolecular 1,1-carboboration of silyl-alkynes has been developed for the synthesis of 2,3-dihydrosilolyl and silylcyclobut-2-enyl boronic esters. Successful, catalytic carboboration has been achieved on a variety of functionally diverse silyl-alkynes, using a borane catalyst and transborylation-enabled turnover. Mechanistic studies, including 13C-labelling, computational studies, and single-turnover experiments, suggest a reaction pathway proceeding by 1,2-hydroboration, 1,1-carboboration, and transborylation to release the alkenyl boronic ester product and regenerate the borane catalyst.

Original languageEnglish
Article numbere202401737
JournalAngewandte Chemie - International Edition
Volume63
Issue number23
Early online date5 Apr 2024
DOIs
Publication statusPublished - 3 Jun 2024

Keywords / Materials (for Non-textual outputs)

  • Boron
  • Catalysis
  • Main group
  • Silicon
  • Transborylation

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