Add time:08/30/2019         Source:sciencedirect.com

The pinacol coupling is one of the most significant methods to synthesize vic-diols. The combination of samarium diiodide (SmI2) and samarium metal successfully induces the selective pinacol couplings of not only aromatic aldehydes and ketones but also aliphatic ones in the presence of trimethylchlorosilane (Me3SiCl) in 1,2-dimethoxyethane (DME). DME is the most suitable solvent for the reduction system using SmI2 and Me3SiCl. Me3SiCl, a widely available additive, prevents the decomposition of the formed vic-diols, i.e., meso-isomers, and controls their stereochemistry. In particular, the pinacol couplings of sterically hindered aliphatic aldehydes and ketones proceed with excellent diastereoselectivities to afford dl-isomers in good yields.

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