Synthesis of Substituted Adamantylzinc Reagents Using a Mg-Insertion in the Presence of ZnCl2 and Further Functionalizations - Research portal of Justus Liebig University Giessen:

Journal article

Synthesis of Substituted Adamantylzinc Reagents Using a Mg-Insertion in the Presence of ZnCl2 and Further Functionalizations

Authors list: Sämann, C; Dhayalan, V; Schreiner, PR; Knochel, P

Publication year: 2014

Pages: 2418-2421

Journal: Organic Letters

Volume number: 16

Issue number: 9

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

Publisher: 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.

Authors/Editors

- Uni.-Prof. Dr. Peter Richard Schreiner, PhD

Citation Styles

Harvard Citation style: 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 Citation style: 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