Sodium Dispersion Applicable to Organic Synthesis

Sodium dispersions including SD Super Fine™ (1) have been used for the dechlorination of polychlorobiphenyls (PCBs) within industry. In recent years, many its application to organic synthesis such as Bouveault−Blanc reductions¹⁾ and the reduction of tertiary amides²⁾ have been reported. For instance, Takai et al. reported a simple preparation of organosodium compounds from organic chlorides and 1 for cross-coupling reactions.³⁾ Organosodium compounds transmetallate with boron and zinc reagents to form organozinc and organoboron intermediates respectively. These intermediates can be readily applied to Negishi and Suzuki-Miyaura cross-coupling in the one-pot manner. In addition, the direct cross-coupling of arylsodiums and arylhalides can be achieved (Scheme 1). Takai et al. also developed lithium-free preparations of NaTMP (2) using 1 via method A and method B (Scheme 2).⁴⁾ 2 has proven to be effective for Wittig reactions, double-bond isomerizations, and functionalization of heteroarenes. In addition, Mori et al. have reported the preparation of anhydrous solvents using 1 as a dehydrating agent.⁵⁾ Owing to its large surface area, less reagent and time is required for dehydration, as well as a simplified quenching compared to large sodium lumps.

Scheme 1 Preparation of organosodium compounds using 1 and its application to cross-coupling reactions

Scheme 2 Preparation of NaTMP using 1

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