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Hammann, Jeffrey M.; Haas, Diana; Tüllmann, Carl-Phillip; Karaghiosoff, Konstantin; Knochel, Paul (2016): Diastereoselective Cobalt-Mediated Cross-Couplings of Cycloalkyl Iodides with Alkynyl or (Hetero)Aryl Grignard Reagents. In: Organic Letters, Vol. 18, No. 19: pp. 4778-4781
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A highly diastereoselective cross-coupling of variously substituted cycloalkyl iodides with alkynyl and (hetero)aryl Grignard reagents using cobalt(II) chloride has been successfully developed. With the THF-soluble CoCl2 center dot LiCl and the inexpensive ortho-phenanthroline derivative, neocuproine, as a ligand, diastereomeric ratios of up to 99:1 were achieved. A range of functional groups are tolerated in the Grignard reagent (e.g., CF3, Piy, CN, OPiv, NMe2, CO2NEt2, SF5, OTBS).