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

Autor:	Vasudevan Dhayalan, Christoph Sämann, Paul Knochel, Peter R. Schreiner
Rok vydání:	2014
Předmět:	chemistry.chemical_compound Terthiophene chemistry Negishi coupling Reagent Organic Chemistry Lipophilicity Organic chemistry Moiety Physical and Theoretical Chemistry Solubility Biochemistry
Zdroj:	Organic Letters. 16:2418-2421
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol500781j
Popis:	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(I)-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 α-substituent in terthiophene, increasing its solubility due to the higher lipophilicity and the prevention of π-stacking.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::193aa28fe4cbd46cd452cef355a26f40 https://doi.org/10.1021/ol500781j Zobrazit plný text záznamu