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).
|Number of pages||5|
|Journal||Angewandte Chemie - International Edition|
|Early online date||1 Jun 2018|
|Publication status||Published - 13 Aug 2018|
- cooperative effects
- transition-metal free
ASJC Scopus subject areas