Journalartikel

Jahr der Veröffentlichung: 2014

Seiten: 2418-2421

Zeitschrift: Organic Letters

Bandnummer: 16

Heftnummer: 9

DOI Link: https://doi.org/10.1021/ol500781j

Verlag: American Chemical Society

Abstract: 

The LiCl-mediated Mg-insertion in the presence of ZnCl2 allows an efficient synthesis of adamantylzinc reagents starting from the corresponding functionalized tertiary bromides. The highly reactive adamantylzinc species readily undergo a broad variety of functionalizations such as Negishi cross-couplings, Cu(1)-catalyzed acylations and allylations, and 1,4-addition reactions leading to the expected products in excellent yields. Furthermore, the adamantyl moiety could be introduced as alpha-substituent in terthiophene, increasing its solubility due to the higher lipophilicity and the prevention of it-stacking.

Harvard-Zitierstil: Sämann, C., Dhayalan, V., Schreiner, P. and Knochel, P. (2014) Synthesis of Substituted Adamantylzinc Reagents Using a Mg-Insertion in the Presence of ZnCl2 and Further Functionalizations, Organic Letters, 16(9), pp. 2418-2421. https://doi.org/10.1021/ol500781j

APA-Zitierstil: Sämann, C., Dhayalan, V., Schreiner, P., & Knochel, P. (2014). Synthesis of Substituted Adamantylzinc Reagents Using a Mg-Insertion in the Presence of ZnCl2 and Further Functionalizations. Organic Letters. 16(9), 2418-2421. https://doi.org/10.1021/ol500781j