Haloboration of internal alkynes with boronium and borenium cations as a route to tetrasubstituted alkenes

James R. Lawson, Ewan R. Clark, Ian A. Cade, Sophia A. Solomon, Michael J. Ingleson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Hail boration! 2-Dimethylaminopyridine-ligated dihaloborocations [X 2B(2-DMAP)]+ with a strained four-membered boracycle were used for the haloboration of terminal and dialkyl internal alkynes (see scheme). Esterification then provided vinyl boronate esters as useful precursors to tetrasubstituted alkenes. Following mechanistic studies, the scope of the haloboration was expanded simply by variation of the amine. Pin=2,3-dimethyl-2, 3-butanedioxy.

Original languageEnglish
Pages (from-to)7518-7522
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number29
DOIs
Publication statusPublished - 15 Jul 2013

Keywords

  • borenium ions
  • boronate esters
  • haloboration
  • synthetic methods
  • tetrasubstituted alkenes

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