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 language | English |
---|---|
Pages (from-to) | 10630-10634 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 57 |
Issue number | 33 |
Early online date | 1 Jun 2018 |
DOIs | |
Publication status | Published - 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
- General Chemistry