Stereoselective Desymmetrization of gem-Diborylalkanes by “Trifluorination”

Nivesh Kumar, Reddy Rajasekhar Reddy, Ahmad Masarwa*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

An efficient and general method for the chemoselective synthesis of unsymmetrical gem-diborylalkanes is reported. This method is based on a late-stage desymmetrization through nucleophilic “trifluorination”, providing chiral gem-diborylalkanes bearing a trifluoroborate group. The reaction offers a highly modular and diastereoselective approach towards the synthesis of gem-diborylcyclopropanes. The utility of the gem-diborylalkane building blocks was demonstrated by selective post-functionalization of the trifluoroborate group. These functionalizations include inter- and intra- Pd-catalyzed Suzuki–Miyaura coupling reactions.

Original languageAmerican English
Pages (from-to)8008-8012
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number34
DOIs
StatePublished - 18 Jun 2019

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Suzuki–Miyaura cross-coupling
  • cyclopropanes
  • desymmetrization
  • gem-diborylalkanes
  • organotrifluoroborate salts

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