874480-23-6Relevant academic research and scientific papers
Synthesis of Polyfunctional Diorganomagnesium and Diorganozinc Reagents through In Situ Trapping Halogen–Lithium Exchange of Highly Functionalized (Hetero)aryl Halides in Continuous Flow
Ketels, Marthe,Ganiek, Maximilian A.,Weidmann, Niels,Knochel, Paul
supporting information, p. 12770 - 12773 (2017/09/13)
We report a halogen–lithium exchange performed in the presence of various metal salts (ZnCl2, MgCl2?LiCl) on a broad range of sensitive bromo- or iodo(hetero)arenes using BuLi or PhLi as the exchange reagent and a commercially available continuous-flow setup. The resulting diarylmagnesium or diarylzinc species were trapped with various electrophiles, resulting in the formation of polyfunctional (hetero)arenes in high yields. This method enables the functionalization of (hetero)arenes containing highly sensitive groups such as an isothiocyanate, nitro, azide, or ester. A straightforward scale-up was possible without further optimization.
Facially selective cu-catalyzed carbozincation of cyclopropenes using arylzinc reagents formed by sequential I/Mg/Zn exchange
Tarwade, Vinod,Selvaraj, Ramajeyam,Fox, Joseph M.
, p. 9900 - 9904 (2013/01/15)
Described is a Cu-catalyzed directed carbozincation of cyclopropenes with organozinc reagents prepared by I/Mg/Zn exchange. This protocol broadens the scope with respect to functional group tolerance and enables use of aryl iodide precursors, rather than purified diorganozinc precursors. Critical to diastereoselectivity of the carbozincation step is the removal of magnesium halide salts after transmetalation with ZnCl2.
