A wide range of polyfunctional diaryl-and diheteroarylzinc species were prepared in toluene within 10 min to 5 h through an I/Zn or Br/Zn exchange reaction using bimetallic reagents of the general formula R’2Zn·2LiOR (R’=sBu, tBu, pTol). Highly sensitive functional groups, such as a triazine, a ketone, an aldehyde, or a nitro group, were tolerated in these exchange reactions, enabling the synthesis of a plethora of functionalized (hetero)arenes after quenching with various electrophiles. Insight into the constitution and reactivity of these bimetallic mixtures revealed the formation of highly active lithium diorganodialkoxyzincates of type[R’2Zn-(OR)2Li2].
- metal/halogen exchange
- organozinc reagents
Balkenhohl, M., Ziegler, D. S., Desaintjean, A., Bole, L. J., Kennedy, A. R., Hevia, E., & Knochel, P. (2019). Preparation of polyfunctional arylzinc organometallics in toluene by halogen/zinc exchange reactions. Angewandte Chemie International Edition, 58(37), 12898-12902. https://doi.org/10.1002/anie.201906898