title: Synthesis of substituted adamantylzinc reagents using a Mg-insertion in the presence of ZnCl₂ and further functionalizations.
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(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.
authors.affiliation: Department of Chemistry, Ludwig-Maximilians-Universität , Butenandtstr. 5-13, 81377 Munich, Germany.
authors.forename: Christoph
authors.initials: C
authors.lastname: Sämann
authors.forename: Vasudevan
authors.initials: V
authors.lastname: Dhayalan
authors.forename: Peter R
authors.initials: PR
authors.lastname: Schreiner
authors.forename: Paul
authors.initials: P
authors.lastname: Knochel
mesh_terms: D000547:Amantadine / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D007202:Indicators and Reagents / Q000138:chemical synthesis* / Q000737:chemistry; D018021:Lithium Chloride / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D017967:Zinc Compounds / Q000737:chemistry*
chemical_list: D002712:Chlorides; D007202:Indicators and Reagents; D017967:Zinc Compounds; C016837:zinc chloride; D000547:Amantadine; D018021:Lithium Chloride; D008274:Magnesium