Exploiting Synergistic Effects in Organozinc Chemistry for Direct Stereoselective C-Glycosylation Reactions at Room Temperature

Alberto Hernán-Gómez, Samantha A. Orr, Marina Uzelac, Alan R. Kennedy, Santiago Barroso, Xavier Jusseau, Sébastien Lemaire, Vittorio Farina, Eva Hevia

Research output: Contribution to journalArticlepeer-review

13 Citations (SciVal)

Abstract

Pairing a range of bis(aryl) zinc reagents ZnAr2 with the stronger Lewis acidic [(ZnArF 2)] (ArF=C6F5), enables highly stereoselective cross-coupling between glycosyl bromides and ZnAr2 without the use of a transition metal. Reactions occur at room temperature with excellent levels of stereoselectivity, where ZnArF 2 acts as a non-coupling partner although its presence is crucial for the execution of the C(sp2)–C(sp3) bond formation process. Mechanistic studies have uncovered a unique synergistic partnership between the two zinc reagents, which circumvents the need for transition-metal catalysis or forcing reaction conditions. Key to the success of the coupling is the avoidance of solvents that act as Lewis bases versus diarylzinc compounds (e.g. THF).

Original languageEnglish
Pages (from-to)10630-10634
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number33
Early online date1 Jun 2018
DOIs
Publication statusPublished - 13 Aug 2018

Bibliographical note

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • arylation
  • cooperative effects
  • transition-metal free
  • zinc
  • zincate

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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