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Diastereoselective Cobalt-Mediated Cross-Couplings of Cycloalkyl Iodides with Alkynyl or (Hetero)Aryl Grignard Reagents.

Organic Letters 2016 October 8
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 ·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 , Piv, CN, OPiv, NMe2 , CO2 NEt2 , SF5 , OTBS).

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