Zwitterion-Initiated Hydroboration of Alkynes and Styrene

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Abstract

The hydroboration of alkynes and styrene with HBpin has been developed using tris(pentaflurophenyl)borane (B(C6F5)3) as the initiator of catalysis. The hydroboration is proposed to be initiated by Lewis acid activation of the alkyne by (B(C6F5)3) to form a highly reactive zwitterionic species which subsequently react with HBpin to give the alkenyl boronic ester. This zwitterion has also showed potential to be a competent catalyst for the hydroboration of styrene. The zwitterionic intermediate is analogous to that proposed in the Piers borane-catalysed hydroboration and 1,1-carboboration of alkynes with B(C6F5)3. 

Original languageEnglish
Article number363
Number of pages5
JournalAdvanced Synthesis and Catalysis
Early online date7 Jan 2021
DOIs
Publication statusE-pub ahead of print - 7 Jan 2021

Keywords

  • alkyne
  • homogeneous catalysis
  • hydroboration
  • main-group chemistry
  • Zwitterion

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